US20190159456A1 - Star polymers with enhanced antimicrobial activity in response to light - Google Patents
Star polymers with enhanced antimicrobial activity in response to light Download PDFInfo
- Publication number
- US20190159456A1 US20190159456A1 US15/824,250 US201715824250A US2019159456A1 US 20190159456 A1 US20190159456 A1 US 20190159456A1 US 201715824250 A US201715824250 A US 201715824250A US 2019159456 A1 US2019159456 A1 US 2019159456A1
- Authority
- US
- United States
- Prior art keywords
- cation
- polymer
- group
- singlet oxygen
- polycarbonate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 199
- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 47
- 230000004044 response Effects 0.000 title claims description 12
- 239000004417 polycarbonate Substances 0.000 claims abstract description 132
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 132
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 111
- 238000000034 method Methods 0.000 claims abstract description 66
- 150000001768 cations Chemical class 0.000 claims abstract description 24
- 125000000524 functional group Chemical group 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 59
- -1 primary amine cation Chemical class 0.000 claims description 52
- 125000002091 cationic group Chemical group 0.000 claims description 42
- 244000052769 pathogen Species 0.000 claims description 38
- 230000001717 pathogenic effect Effects 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 34
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 22
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 22
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 18
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 18
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 14
- 241000894006 Bacteria Species 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 11
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 11
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 11
- 229950000688 phenothiazine Drugs 0.000 claims description 11
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000004032 porphyrins Chemical class 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 239000012528 membrane Substances 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 9
- 241000192125 Firmicutes Species 0.000 claims description 9
- 241000233866 Fungi Species 0.000 claims description 9
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 8
- 125000001165 hydrophobic group Chemical group 0.000 claims description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 231100000331 toxic Toxicity 0.000 claims description 6
- 230000002588 toxic effect Effects 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003158 alcohol group Chemical group 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 229920001817 Agar Polymers 0.000 description 31
- 239000008272 agar Substances 0.000 description 31
- 238000006116 polymerization reaction Methods 0.000 description 20
- 238000010586 diagram Methods 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- 230000003252 repetitive effect Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 0 *OC(=O)C1(C)COC(=O)OC1 Chemical compound *OC(=O)C1(C)COC(=O)OC1 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000002209 hydrophobic effect Effects 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000003642 reactive oxygen metabolite Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 150000002576 ketones Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 2
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 150000005676 cyclic carbonates Chemical class 0.000 description 2
- 230000009089 cytolysis Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000013467 fragmentation Methods 0.000 description 2
- 238000006062 fragmentation reaction Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 208000037408 Device failure Diseases 0.000 description 1
- 239000012988 Dithioester Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZYKJMNKVKCHYPR-UHFFFAOYSA-N [4-(chloromethyl)phenyl]methyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate Chemical compound C=1C=C(CCl)C=CC=1COC(=O)C1(C)COC(=O)OC1 ZYKJMNKVKCHYPR-UHFFFAOYSA-N 0.000 description 1
- DRBMZVXDGASECA-ZRVUXMCASA-N [H]OCC(C)(COC(=O)OCCOC1=CC=C(/C2=C3\C=C/C(=C(\C4=CC=C(OCCOC(=O)OCC(C)(CO[H])C(=O)OCC5=CC=C(C[N+](C)(C)CCCC)C=C5)C=C4)C4=N/C(=C(/C5=CC=C(OCCOC(=O)OCC(C)(CO[H])C(=O)OCC6=CC=C(CN(C)(C)CCCC)C=C6)C=C5)C5=CC=C(C5)/C(C5=CC=C(OCCOC(=O)OCC(C)(CO[H])C(=O)OCC6=CC=C(CN(C)(C)CCCC)C=C6)C=C5)=C5/C=CC2=N5)C=C4)N3)C=C1)C(=O)OCC1=CC=C(CN(C)(C)CCCC)C=C1 Chemical compound [H]OCC(C)(COC(=O)OCCOC1=CC=C(/C2=C3\C=C/C(=C(\C4=CC=C(OCCOC(=O)OCC(C)(CO[H])C(=O)OCC5=CC=C(C[N+](C)(C)CCCC)C=C5)C=C4)C4=N/C(=C(/C5=CC=C(OCCOC(=O)OCC(C)(CO[H])C(=O)OCC6=CC=C(CN(C)(C)CCCC)C=C6)C=C5)C5=CC=C(C5)/C(C5=CC=C(OCCOC(=O)OCC(C)(CO[H])C(=O)OCC6=CC=C(CN(C)(C)CCCC)C=C6)C=C5)=C5/C=CC2=N5)C=C4)N3)C=C1)C(=O)OCC1=CC=C(CN(C)(C)CCCC)C=C1 DRBMZVXDGASECA-ZRVUXMCASA-N 0.000 description 1
- URLCZUREVWCQLT-UHFFFAOYSA-N [H]OCC(C)(COC(C)=O)C(=O)OCC1=CC=C(CC)C=C1 Chemical compound [H]OCC(C)(COC(C)=O)C(=O)OCC1=CC=C(CC)C=C1 URLCZUREVWCQLT-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- VFHDWGAEEDVVPD-UHFFFAOYSA-N chembl507897 Chemical compound C1=CC(O)=CC=C1C(C1=CC=C(N1)C(C=1C=CC(O)=CC=1)=C1C=CC(=N1)C(C=1C=CC(O)=CC=1)=C1C=CC(N1)=C1C=2C=CC(O)=CC=2)=C2N=C1C=C2 VFHDWGAEEDVVPD-UHFFFAOYSA-N 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 125000005022 dithioester group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
- A61L2/23—Solid substances, e.g. granules, powders, blocks, tablets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
- C08G64/0225—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
- C08G64/0241—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
- C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
- C08G64/1641—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
- C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
- C08G64/1658—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/42—Chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D169/00—Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
- A61L2202/20—Targets to be treated
- A61L2202/24—Medical instruments, e.g. endoscopes, catheters, sharps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
- A61L2202/20—Targets to be treated
- A61L2202/25—Rooms in buildings, passenger compartments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
- A61L2202/20—Targets to be treated
- A61L2202/26—Textiles, e.g. towels, beds, cloths
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/003—Dendrimers
- C08G83/004—After treatment of dendrimers
Definitions
- the subject disclosure relates to a star polymer with antimicrobial activity, and more specifically, to a star polymer that can exhibit enhanced antimicrobial activity in response to light.
- compositions and methods regarding star polymers that can exhibit enhanced antimicrobial activity in response to light are described.
- a polymer can comprise a core that can have a singlet oxygen generator and that can generate a singlet oxygen species upon irradiation with light.
- the polymer can further comprise a plurality of polycarbonate arms covalently bonded to the core.
- the plurality of polycarbonate arms can be degradable and can comprise a cation. Further, the plurality of polycarbonate arms can have antimicrobial functionality.
- a method can comprise forming a plurality of degradable polycarbonate arms by polymerizing a plurality of carbonates with a singlet oxygen generator core.
- the singlet oxygen generator core can generate a singlet oxygen species in response to being irradiated with light.
- the method can also comprise generating a cationic moiety by covalently bonding a functional group with a degradable polycarbonate arm from the plurality of degradable polycarbonate arms.
- a film-forming composition can comprise a solvent and a polymer.
- the polymer can comprise greater than or equal to 5 weight percent of the film-forming composition and less than or equal to 20 weight percent of the film-forming composition. Further, the polymer can be dispersed in the solvent.
- the polymer can also comprise a core that can have a singlet oxygen generator and that can generate a singlet oxygen species upon irradiation with light.
- the polymer can further comprise a plurality of polycarbonate arms covalently bonded to the core. The plurality of polycarbonate arms can be degradable and can comprise a cation. Moreover, the plurality of polycarbonate arms can have antimicrobial functionality.
- a method of forming a surface treated article can comprise disposing on a surface of an article a film-forming composition.
- the film-forming composition can comprise a solvent and a polymer.
- the polymer can comprise greater than or equal to 5 weight percent of the film-forming composition and less than or equal to 20 weight percent of the film-forming composition. Further, the polymer can be dispersed in the solvent.
- the polymer can also comprise a core that can have a singlet oxygen generator and that can generate a singlet oxygen species upon irradiation with light.
- the polymer can further comprise a plurality of polycarbonate arms covalently bonded to the core.
- the plurality of polycarbonate arms can be degradable and can comprise a cation. Moreover, the plurality of polycarbonate arms can have antimicrobial functionality.
- the method can additionally comprise removing the solvent from the surface of the article.
- a method of killing a pathogen can comprise contacting the pathogen with a polymer.
- the polymer can comprise a core that can have a singlet oxygen generator and that can generate a singlet oxygen species upon irradiation with light.
- the polymer can further comprise a plurality of polycarbonate arms covalently bonded to the core.
- the plurality of polycarbonate arms can be degradable and can comprise a cation. Further, the plurality of polycarbonate arms can have antimicrobial functionality.
- the contacting of the pathogen with the polymer can electrostatically disrupt a membrane of the pathogen.
- FIG. 1 illustrates a diagram of an example, non-limiting star polymer in accordance with one or more embodiments described herein.
- FIG. 2 illustrates a diagram of an example, non-limiting arm from a plurality of arms that can comprise a star polymer in accordance with one or more embodiments described herein.
- FIG. 3 illustrates a diagram of an example, non-limiting singlet oxygen generator core that can comprise a star polymer in accordance with one or more embodiments described herein.
- FIG. 4 illustrates a flow diagram of an example, non-limiting method that can facilitate generation of a star polymer in accordance with one or more embodiments described herein.
- FIG. 5 illustrates a diagram of an example, non-limiting scheme that can facilitate generation of a star polymer in accordance with one or more embodiments described herein.
- FIG. 6 illustrates a diagram of an example, non-limiting chart that can demonstrate a composition of a star polymer generated in accordance with one or more embodiments described herein.
- FIG. 7 illustrates four photos of example, non-limiting agar plates that can demonstrate the antimicrobial efficacy of a star polymer in accordance with one or more embodiments described herein.
- FIG. 8 illustrates a diagram of an example, non-limiting bar graph that can demonstrate the antimicrobial efficacy of a star polymer in accordance with one or more embodiments described herein.
- FIG. 9 illustrates another flow diagram of an example, non-limiting method that can facilitate treating a surface of an article with a film-forming composition in accordance with one or more embodiments described herein.
- FIG. 10 illustrates another flow diagram of an example, non-limiting method that can facilitate killing a pathogen through contact with a star polymer in accordance with one or more embodiments described herein.
- biofilms can form on human tissue and implanted devices, leading to implant failure.
- the biofilms can be composed of bacteria embedded within a self-produced extracellular polymeric matrix.
- the biofilms can be difficult to penetrate, thereby rendering it difficult to kill the embedded bacteria.
- ROS reactive oxygen species
- pathogens such as, but not limited to: Gram-positive bacteria, Gram-negative bacteria, fungi, and yeast.
- ROS can be effective in cleansing and/or treating stagnate wounds and treating chronic obstructive pulmonary disease.
- ROS can be toxic to various pathogens, they can be equally as toxic against host cells.
- conventional ROS can be unstable and exhibit undesirable burst releases.
- compositions e.g., film-forming compositions
- methods for the synthesis and/or use of antimicrobial star polymers with enhanced activity provided by light activated singlet oxygen generating functionalities can refer to a polymer having a plurality of arms, which can be crosslinked, branching from a discrete core.
- star polymer can refer to a polymer having a plurality of arms, which can be crosslinked, branching from a discrete core.
- a film-forming composition can comprise the polymer compositions described herein.
- one or embodiments can regard methods utilizing the polymer composition and/or film-forming composition to kill, and/or prevent contamination and/or growth of, various pathogens (e.g., Gram-positive bacteria, Gram-negative bacteria, fungi, and yeast) and/or surface treat various articles (e.g., food and/or medical packaging).
- various pathogens e.g., Gram-positive bacteria, Gram-negative bacteria, fungi, and yeast
- various articles e.g., food and/or medical packaging.
- FIG. 1 illustrates a diagram of an example, non-limiting star polymer 100 in accordance with one or more embodiments described herein.
- the star polymer 100 can comprise a plurality of polycarbonate arms 102 covalently bonded to a singlet oxygen generator core 104 .
- the star polymer 100 can crosslink with one or more additional star polymers (e.g., star polymer 100 ) without the assistance of an additional chemical crosslinking agent and/or photochemical activation.
- the crosslinking can be chemical (e.g., covalent bonds), physical (e.g., hydrophobic bonding, chain entanglement, and/or ionic association), and/or a combination thereof.
- the plurality of polycarbonate arms 102 can be present in the star polymer 100 as homopolymers, random copolymers, block polymers, and/or a combination thereof.
- the star polymer 100 can comprise one or more functionalization sites that can be utilized to control chemical interactions that can facilitate antimicrobial and/or film-forming properties.
- plurality of the polycarbonate arms 102 and/or the singlet oxygen generator core 104 can be capable of further chain growth.
- FIG. 2 illustrates a drawing of an example, non-limiting polycarbonate arm 102 of the plurality of polycarbonate arms 102 that can comprise the star polymer 100 .
- each polycarbonate arm 102 from the plurality of polycarbonate arms 102 can be characterized by the same structure.
- one or more polycarbonate arms 102 of the star polymer 100 can exhibit the features described herein via a chemical structure different than one or more other polycarbonate arms 102 of the star polymer 100 .
- the plurality of polycarbonate arms 102 can comprise four polycarbonate arms 102 .
- the polycarbonate arm 102 can have a positive charge when bonded to the singlet oxygen generator core 104 .
- the polycarbonate arm 102 can comprise a molecular backbone 202 covalently bonded to the singlet oxygen generator core 104 .
- the polycarbonate arm 102 can comprise a cationic functional group 204 covalently bonded to the molecular backbone 202 .
- the polycarbonate arm 102 can further comprise a reactive end group 206 covalently bonded to the molecular backbone 202 .
- FIG. 2 delineates that the polycarbonate arm's 102 molecular backbone 202 can be bonded to the singlet oxygen generator core 104 .
- FIG. 2 illustrates an exemplary structure; however, alternate structures are also envisaged.
- Example chemical structures comprising the molecular backbone 202 can include, but are not limited to: alkyl structures, aryl structures, alkane structures, aldehyde structures, ether structures, ketone structures, ester structures, carboxyl structures, carbonyl structures, amine structures, amide structures, phosphide structures, phosphine structures, a combination thereof, and/or the like.
- the size of the molecular backbone 202 can vary depending of the desired function of the star polymer 100 . For example, “n” can represent an integer great than or equal to 5 and less than or equal to 1000.
- the molecular backbone 202 can be covalently bonded to the cationic functional group 204 (e.g., illustrated in FIG. 2 as “R”).
- the cationic functional group 204 can be bonded to the molecular backbone 202 via a first linkage group 208 .
- FIG. 2 illustrates the first linkage group 208 having an ester structure; however other chemical structures are also envisaged.
- Example chemical structures for the first linkage group 208 can include, but are not limited to: alkyl structures, aryl structures, alkane structures, ether structures, carboxyl structures, ketone structures, ester structures, carboxyl structures, carbonyl structures, a combination thereof, and/or the like.
- the first linkage group 208 can be a product of polymerization used to form the polycarbonate arm 102 . In some embodiments, the first linkage group 208 can be a product of post-polymerization of the polycarbonate arm 102 .
- the cationic functional group 204 can comprise one or more nitrogen and/or phosphorus cations.
- Example nitrogen cations can include, but are not limited to: quaternary ammonium cations, protonated primary amine cations, protonated secondary amine cations, protonated tertiary amine cations, and/or imidazolium cations.
- phosphorus cations can include, but are not limited to: quaternary phosphonium cations, protonated primary phosphine cations, protonated secondary phosphine cations, and/or protonated tertiary cations.
- the cationic functional group 204 can comprise a hydrophobic group (e.g., an alkyl group and/or an aryl group) bonded to the one or more nitrogen cations and/or phosphorus cations.
- the nitrogen cations and/or phosphorus cations can be formed via protonation, alkylation, and/or quaternization.
- the polycarbonate arm 102 can further comprise a reactive end group 206 bonded to the molecular backbone 202 .
- the reactive end group 206 can facilitate self-crosslinking of the star polymer 100 with another star polymer (e.g., another star polymer 100 ).
- the reactive end group 206 can comprise a halide ion located alpha to a carbonyl group and/or alpha to an aromatic ring.
- halide ions include: fluoride, chloride, bromide, iodide, and astatide.
- Example carbonyl groups include, but are not limited to: alpha-halo ketones, alpha-halo esters, alpha-halo acids, alpha-halo amides, and/or a combination thereof.
- Example aromatic rings include, but are not limited to: phenyl, pyridinyl, and/or the like.
- the reactive end group 206 can be a product of polymerization used to form the polycarbonate arm 102 .
- the reactive end group 206 can comprise: an epoxide (e.g., from anionic polymerization), an alkoxyamine (e.g., from controlled radical polymerization), a dithioester (e.g., from reversible addition-fragmentation transfer polymerization), and/or a trithiocarbonate (e.g., from reversible addition-fragmentation transfer polymerization).
- the reactive end group 206 can be prepared by chemically modifying the peripheral end of the polycarbonate arm 102 .
- the peripheral end of the polycarbonate arm 102 can be modified to produce a reactive end group 206 including, but not limited to: an azide, a thiol, an olefin, and/or an aryl substituted ketone.
- the polycarbonate arm 102 can be a degradable polycarbonate covalently bonded to a discrete singlet oxygen generator core 104 , and the polycarbonate arm 102 can comprise a molecular backbone 202 bonded to a cationic functional group 204 .
- the cationic functional group 204 can be positively charged (e.g., via one or more nitrogen and/or phosphorus cation) to facilitate antimicrobial functionality.
- the cationic functional group 204 can comprise a hydrophobic group (e.g., bonded to the to one or more nitrogen and/or phosphorus cations), which can further enhance antimicrobial functionality.
- the cationic functional group 204 can be directly bonded to the molecular backbone 202 , and/or the cationic functional group 204 can be bonded to the molecular backbone 202 via a first linkage group 208 (e.g., the first linkage group 208 can be formed as a product of the polymerization of the polycarbonate arm 102 ).
- the molecular backbone 202 can be bonded to a reactive end group 206 , which can facilitate crosslinkage of the star polymer 100 with another star polymer (e.g., star polymer 100 ).
- the plurality of polycarbonate arms 102 can exhibit antimicrobial functionality through a lysis of pathogen cells.
- a membrane of a subject pathogen cell can comprise a phospholipid bilayer.
- the phospholipid bilayer can comprise a plurality of molecules having hydrophilic heads and/or hydrophobic tails. Additionally, one or more of the plurality of membrane molecules can be negatively charged.
- the positive charge of the polycarbonate arm 102 (e.g., via the cationic functional group 204 ) can attract the star polymer 100 to the negatively charged membrane molecules and facilitate cleaving of said molecules from adjacent membrane molecules.
- the hydrophobicity of the polycarbonate arm 102 (e.g., via the cationic functional group 204 ) can further facilitate said cleaving as the hydrophobic group of the cationic functional group 204 integrates itself into the hydrophobic region of the membrane.
- the polycarbonate arm 102 can facilitate a lysis of the pathogen cell through electrostatic disruption and/or hydrophobic membrane integration.
- Example pathogen cells that can be subject to the antimicrobial effects of the polycarbonate arm 102 can include, but are not limited to: Gram-negative bacteria, Gram-positive bacteria, fungi and yeast.
- FIG. 3 illustrates a diagram of an example, non-limiting singlet oxygen generator core 104 that can comprise the star polymer 100 . Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity.
- the plurality of polycarbonate arms 102 can be crosslinked together and/or covalently bonded to the singlet oxygen generator core 104 .
- FIG. 3 shows the singlet oxygen generator core 104 with an exemplary chemical structure derived from a porphyrin; however, other chemical structures are also envisaged.
- the singlet oxygen generator core 104 can have a chemical structure derived from a molecule selected from a group that can include, but is not limited to: a phthalocyanine, a phenothiazine, a xanthene, and/or a quinone.
- the singlet oxygen generator core 104 can comprise one or more second linkage groups 302 (e.g., represented by “L” in FIG. 3 ) that can facilitate bonding the plurality of polycarbonate arms 102 (e.g., represented by “A” in FIG. 3 ) to the singlet oxygen generator core 104 .
- second linkage groups 302 e.g., represented by “L” in FIG. 3
- the second linkage group 302 can be derived from an alcohol and/or an ether (e.g., an alcohol comprising a halide).
- a periphery of the second linkage group 302 can comprise an oxygen atom (e.g., derived from a hydroxyl group) such that a polycarbonate structure is formed by the bonding of an arm 102 and a second linkage group 302 .
- the singlet oxygen generator core 104 can generate one or more singlet oxygen species, which can enhance antimicrobial functionality of the star polymer 100 .
- the star polymer 100 can exhibit enhanced anti-microbial functionality on-demand.
- the singlet oxygen generator core 104 can generate one or more singlet oxygen species in response to light having a wavelength greater than or equal to 10 nanometers (nm) and less than or equal to 750 nm.
- FIG. 4 illustrates a flow diagram of an example, non-limiting method 400 that can facilitate generating the star polymer 100 in accordance with in one or more embodiments described herein. Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity.
- the method 400 can comprise preparing the singlet oxygen generator core 104 by polymerizing a singlet oxygen generator molecule with a first functional group.
- the singlet oxygen generator molecule and the first functional group can be mixed together in a solvent to form a solution.
- the solution can then be heated (e.g., to a temperature greater than or equal to 100 degrees Celsius (° C.) and less than or equal to 200° C.).
- the solution can be agitated (e.g., stirred) for a defined period of time (e.g., greater than or equal to 12 hours and less than or equal to 48 hours).
- the solution can optionally be agitated under nitrogen gas.
- the singlet oxygen generator core 104 can form as a precipitate of the solution.
- Preparing the singlet oxygen generator core 104 can comprise bonding one or more first functional groups to a singlet oxygen generating molecule.
- the singlet oxygen generating molecule can generate one or more singlet oxygen species in response to being irradiated with light (e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm).
- Example singlet oxygen generating molecules can include, but are not limited to: a porphyrin, a phthalocyanine, a phenothiazine, a xanthene, a quinone, and/or the like.
- Example first functional groups can comprise alcohol groups, carboxyl groups, ester groups, and/or one or more halides.
- the one or more first functional groups can facilitate a bonding of the plurality of polycarbonate arms 102 to the singlet oxygen generating molecule and later become the second linkage group 302 when said bonding occurs.
- one or more first functional groups can comprise an alcohol group such that the preparing at 402 results in a singlet oxygen generator core 104 comprising one or more hydroxyl groups that can facilitate the polymerization of a plurality of polycarbonate arms 102 .
- the method 400 can comprise forming a plurality of degradable polycarbonate arms 102 by polymerizing a plurality of carbonates with the prepared singlet oxygen generator core 104 (e.g., in the presence of an organocatylst).
- the plurality of carbonates and the prepared singlet oxygen generator core 104 can be mixed with one or more solvents and/or one or more organocatylsts to form a solution.
- the solution can be agitated (e.g., stirred) at room temperature (“RT”) for a defined period of time (e.g., greater than or equal to 30 minutes and less than or equal to 120 minutes).
- the polymerization at 404 can covalently bond a plurality of carbonates together to form a one or more degradable polycarbonate structures, and/or the polymerization can covalently bond the one or more degradable polycarbonate structures to the prepared singlet oxygen generator core 104 .
- one or more of the carbonates and/or one or more of the polycarbonate structures can comprise a second functional group.
- the second functional group can facilitate later generation of the cationic functional group 204 .
- the second functional group can comprise an alkyl halide.
- Covalently bonding the plurality of carbonates together to form the polycarbonate structure can form the molecular backbone 202 . Further, one or more of the polycarbonate structures can be covalently bonded to the first functional group to facilitate bonding to the prepared singlet oxygen generator core 104 , whereupon the first functional group can become the second linkage group 302 .
- the one or more of the plurality of carbonates can be cyclic carbonates
- the polymerization at 404 can comprise ring-opening polymerization (ROP) of the cyclic carbonates to form a polycarbonate structure (e.g., molecular backbone 202 ).
- ROP ring-opening polymerization
- the one or more carbonates can have a structure characterized by formula 1:
- R 1 can represent the second functional group.
- ROP can form a polycarbonate structure characterized by formula 2:
- R 1 can represent the second functional group
- X can represent a bond to the singlet oxygen generator core 104
- n can represent an integer greater than or equal to 5 and less than or equal to 1000.
- the second functional group can be 4-methylbenzyl chloride, thereby rendering one or more carbonates of 2-oxo-5-methyl-1,3-dioxane-5-carboxylic acid 4-(chloromethyl)benzyl ester (“MTC-OBnCl”).
- the polymerization at 404 can comprise a ROP of the MTC-OBnCl carbonates to form a polycarbonate structure characterized by formula 3:
- the first linkage group 208 is formed as a result of the polymerization at 404 ; however, as described herein, the first linkage group 208 can also be formed post said polymerization at 404 .
- the second functional group can be covalently bonded to one or more of the carbonates prior to the polymerization at 404 ; while in some embodiments the second functional group can be covalently bonded to the polycarbonate structure post polymerization at 404 .
- the method 400 can comprise generating a cationic moiety (e.g. the cationic functional group 204 ) by covalently bonding a third functional group with a degradable polycarbonate arm 102 from the plurality of degradable polycarbonate arms 102 (e.g., polycarbonate structures that can be characterized by molecular backbone 202 ), thereby forming the star polymer 100 .
- the intermediate structure formed at 404 can be mixed with the third functional group in a solvent at RT for a defined period of time (e.g., greater than or equal to one day and less than or equal to three days).
- the solvent can comprise an acetyl group.
- the third functional group can comprise an amine group, an imidazole (e.g., a structure comprising an imidazole ring) and/or a phosphine group.
- generating the cationic moiety (e.g., cationic functional group 204 ) at 406 can comprise covalently bonding the third functional group to a second functional group of a polycarbonate structure formed at 404 .
- the third functional group can be covalently bonded to the second functional group through alkylation and/or quaternization.
- the third functional group can be covalently bonded to the second functional group in the presence of an acetyl group to generate the cationic moiety (e.g., the cationic functional group 204 ).
- the method 400 can comprise preparing (e.g., at 402 ) a singlet oxygen generator core 104 by polymerizing a singlet oxygen generator molecule (e.g., a porphyrin, a phthalocyanine, a phenothiazine, a xanthene, and/or a quinone) with one or more first functional groups (e.g., an alcohol group).
- a singlet oxygen generator molecule e.g., a porphyrin, a phthalocyanine, a phenothiazine, a xanthene, and/or a quinone
- the singlet oxygen generator core 104 can generate a singlet oxygen species in response to light (e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm).
- the method 400 can comprise forming (e.g., at 404 ) a plurality of degradable polycarbonate structures (e.g., characterized by molecular backbone 202 ) by polymerizing a plurality of carbonates with the singlet oxygen generator core 104 (e.g., in the presence of an organocatalyst).
- the polymerization can covalently bond the plurality of carbonates together to form the one or more polycarbonate structures (e.g., characterized by the molecular backbone 202 of a plurality of degradable polycarbonate arms 102 ).
- the polymerization can also form one or more second functional groups bonded to the one or more polycarbonate structures, wherein the second functional groups (e.g., an alkyl halide) can facilitate generation of one or more cationic moieties. Further, the polymerization can covalently bond the one or more polycarbonate structures to the singlet oxygen generator core 104 via the first functional group, whereupon the first functional group can thereby transform into a linkage group (e.g., second linkage group 302 ).
- a linkage group e.g., second linkage group 302
- the method 400 can comprise generating (e.g., at 406 ) one or more cation moieties (e.g., cationic functional group 204 ) by covalently bonding one or more third functional groups (e.g., an amine group, an imidazole group, and/or a phosphine group) with one or more of the polycarbonate structures to form a plurality of positively charged degradable polycarbonates (e.g., polycarbonate arms 102 ), and thereby a star polymer (e.g., star polymer 100 ).
- one or more cation moieties e.g., cationic functional group 204
- third functional groups e.g., an amine group, an imidazole group, and/or a phosphine group
- Generating the one or more cationic moieties can comprise an alkylation and/or quaternization of the third functional group with the second functional group to generate the one or more cationic moieties (e.g., cation functional group 204 ), whereupon the second functional group can thereby transform into another linkage group (e.g., first linkage group 208 ).
- the one or more cationic moieties can comprise a nitrogen cation (e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation) and/or a phosphorus cation (e.g., a protonated primary phosphine cation, a protonated secondary phosphine cation, a protonated tertiary phosphine cation, a quaternary phosphonium cation).
- a nitrogen cation e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation
- the one or more of the generated cation moieties can further comprise a hydrophobic functional group (e.g., bonded to the nitrogen cation and/or the phosphorus cation).
- the polymerized degradable polycarbonates e.g., polycarbonate arms 102
- can comprise a reactive functional group e.g., reactive end group 206 to facilitate crosslinkage of the star polymer (e.g., star polymer 100 ) with another star polymer (e.g., another star polymer 100 ).
- FIG. 5 illustrates a diagram of an example, non-limiting scheme 500 that can exemplify the formation of a star polymer 100 in accordance with one or more embodiments described herein (e.g., method 400 ). Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity.
- the scheme 500 can depict a preparation of the singlet oxygen generator core 104 (e.g., in accordance with 402 of method 400 ).
- TPP 5,10,15,20-Tetrakis(4hydroxyphenyl)porphyrin
- DMF dimethylformamide
- the ethanol can serve as the first functional group, thereby providing a hydroxyl group to facilitate covalent bonding of one or more polycarbonate structures (e.g., molecular backbone 202 ).
- the scheme 500 can depict forming the plurality of degradable polycarbonate structures (e.g., characterized by molecular backbone 202 ) by polymerizing a plurality of carbonates with the singlet oxygen generator core 104 in an organocatlyst (e.g., in accordance with 404 of method 400 ).
- the hydroxyl-TPP can be polymerized with a plurality of MTC-OBnCl carbonates in the presence of dichloromethane (“DCM”), 1,8-diazabicyclo[5.4.0]undec-7-ene (“DBU”), and 1-1-[3,5-bis(trifluoromethyl)-phenyl]-3-cyclohexyl-2-thiourea (“TU”) for defined period of time (e.g., two hours).
- DCM dichloromethane
- DBU 1,8-diazabicyclo[5.4.0]undec-7-ene
- TU 1-cyclohexyl-2-thiourea
- the polycarbonate structures can covalently bond to one or more of the hydroxyl groups of the hydroxyl-TPP; thereby transforming the one or more first functional groups into the one or more second linkage groups 302 .
- the 4-methylbenzyl chloride functional group of the carbonates can serve as the second functional group, which can facilitate generating the cationic moiety.
- the polymerization at 504 can produce an intermediate structure in the scheme 500 .
- the scheme 500 can depict a generation of one or more cationic moieties (e.g., cationic functional group 204 ) by covalently bonding one or more third functional groups with one or more of the degradable polycarbonate structures (e.g., in accordance with 406 of method 400 ).
- the intermediate structure can be mixed with dimethylbutylamine in acetonitrile (“AcCN”) to form a solution.
- the solution can be agitated (e.g., stirred) at RT for a defined period of time (e.g., greater than or equal to 1 hour and less than or equal to 6 hours).
- the dimethylbutylamine can serve as the third functional group, and quaternization of the dimethylbutylamine can bond the dimethylbutylamine to the second functional group and form a nitrogen cation (e.g., a quaternary ammonium cation), thereby installing a positive charge to the plurality of polycarbonate arms 102 .
- the solvent can be removed from the solution and a dialysis can be performed to retrieve the product (e.g., the star polymer 100 ).
- the dialysis can be carried out over a defined period of time (e.g., greater than or equal to one day and less than or equal to three days) at RT using 1:1 alcohol and acetonitrile.
- FIG. 6 illustrates a diagram of an example, non-limiting chart 600 that can confirm the structure of a star polymer 100 created by scheme 500 in accordance with one or more embodiments described herein (e.g., method 400 ). Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity.
- a star polymer 100 can be generated in accordance with method 400 and/or scheme 500 .
- 200 milligrams (mg) of 0.029 millimole (mmol) TPP can be charged in a 50 milliliter (mL) flask equipped with a stir bar with 501 mg of 3.63 mmol potassium carbonate and 8.61 microliters ( ⁇ L) of 0.044 mmol 15-crown-5 in 25 mL of DMF.
- the reaction mixture can be stirred for 15 minutes at RT before 185 ⁇ L of 2.61 mmol 2-bromoethanol can be added in a dropwise fashion. Subsequently, the mixture can be heated at 140° C. and stirred under nitrogen for 24 hours.
- the solvent can be removed under vacuum and the residual solids can be dissolved in 25 mL of tetrahydrofuran (“THF”).
- THF tetrahydrofuran
- An organic layer can then be extracted twice with 15 mL of water, once with 15 mL of brine, and dried over sodium sulfate.
- the solvent can be removed and the crude product can be re-dissolved in 5 mL of THF.
- a precipitation in cold diethyl ether can follow. The precipitate can be filtered and placed under vacuum for 18 hours, whereupon the final product can be hydroxyl-TPP.
- 4.3 mg of 0.005 mmol hydroxyl-TPP and 150 mg of 0.5 mmol MTC-OBnCl can be placed in a 20 mL glass vial equipped with a stir bar. Additionally, DCM can be added to the glass vial to ensure all solids are dissolved. The monomer concentration can be calibrated to 2 moles per liter (M). After which, 3.7 ⁇ L of 0.025 mmol DBU and 9.3 mg of 0.025 mmol TU can be added to initiate polymerization. The mixture can be stirred at RT for 1.5 hours. Next, 30 mg of benzoic acid can be added to the mixture to quench the reaction. Subsequently, the polymer intermediate can be purified via precipitation in cold diethyl ether and dried under vacuum.
- the polymer intermediate can then be dissolved in 2 mL of acetonitrile and subsequently, quaternized with 750 ⁇ L of dimethylbutylamine at RT with stirring for 4.5 hours.
- the solvent can be removed under vacuum and the quaternized polymer can be dissolved in 4 mL of isopropanol and acetonitrile mixture having a 1:1 ratio.
- the solution can be placed within a dialysis bag of 1000 molecular weight cut-off. Dialysis can be carried for two days at RT using 1:1 isopropanol and acetonitrile.
- the solvents can be removed and the polymer lyophilized to obtain a star polymer 100 product.
- the chemical structure of the star polymer 100 product can then be analyzed using proton nuclear magnetic resonance ( 1 H NMR) to generate chart 600 .
- Chart 600 illustrates that the polymer generated in accordance with one or more embodiments described herein (e.g., method 400 and/or scheme 500 ) can exhibit the features of a star polymer 100 described herein.
- the 1 H NMR spectra can be recorded at RT using standard Bruker library pulse programs. Further, analytical permeation chromatography (GPC) and/or dynamic light scattering (LS) measurements can be conducted.
- GPS analytical permeation chromatography
- LS dynamic light scattering
- FIG. 7 illustrates eight photos of example, non-limiting agar plates used to demonstrate the antimicrobial efficacy of the star polymer 100 .
- Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity.
- the eight photos are illustrated in pairs to demonstrate the effect of irradiating the star polymer 100 with light at varying concentrations.
- Each of the agar plates shown in FIG. 7 comprise a growth solution, a bacterial culture of Pseudomonas aeruginosa , and a concentration of the star polymer 100 formed in accordance with method 400 and/or scheme 500 and analyzed by chart 600 .
- the first photo pair 702 can regard agar plates comprising the star polymer 100 at a 16 micrograms per milliliter ( ⁇ g/mL) concentration.
- the first agar plate 704 can depict the antimicrobial functionality of the star polymer 100 at 16 ⁇ g/mL, wherein the star polymer 100 is not irradiated with light.
- the second agar plate 706 can depict the antimicrobial functionality of the star polymer 100 at 16 ⁇ g/mL, wherein the star polymer 100 is irradiated with light.
- the second photo pair 708 can regard agar plates comprising the star polymer 100 at a 31 micrograms per milliliter ( ⁇ g/mL) concentration.
- the third agar plate 710 can depict the antimicrobial functionality of the star polymer 100 at 31 ⁇ g/mL, wherein the star polymer 100 is not irradiated with light.
- the fourth agar plate 712 can depict the antimicrobial functionality of the star polymer 100 at 31 ⁇ g/mL, wherein the star polymer 100 is irradiated with light.
- the third photo pair 714 can regard agar plates comprising the star polymer 100 at a 63 micrograms per milliliter ( ⁇ g/mL) concentration.
- the fifth agar plate 716 can depict the antimicrobial functionality of the star polymer 100 at 63 ⁇ g/mL, wherein the star polymer 100 is not irradiated with light.
- the sixth agar plate 718 can depict the antimicrobial functionality of the star polymer 100 at 63 ⁇ g/mL, wherein the star polymer 100 is irradiated with light.
- the fourth photo pair 720 can regard agar plates comprising the star polymer 100 at a 125 micrograms per milliliter ( ⁇ g/mL) concentration.
- the seventh agar plate 722 can depict the antimicrobial functionality of the star polymer 100 at 125 ⁇ g/mL, wherein the star polymer 100 is not irradiated with light.
- the eighth agar plate 724 can depict the antimicrobial functionality of the star polymer 100 at 125 ⁇ g/mL, wherein the star polymer 100 is irradiated with light.
- FIG. 8 illustrates a diagram of an example, non-limiting bar graph 800 that analytically exemplifies the antimicrobial effect of each of the agar plates depicted in FIG. 7 . Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity.
- the first bar 802 can regard the first agar plate 704 ; the second bar 804 can regard the second agar plate 706 ; the third bar 806 can regard the third agar plate 710 ; the fourth bar 808 can regard the fourth agar plate 712 ; the fifth bar 810 can regard the fifth agar plate 716 ; the sixth bar 812 can regard the sixth agar plate 718 ; seventh bar 814 can regard the seventh agar plate 722 ; and the eighth bar 816 can regard the eighth agar plate 724 .
- the visual appearance of antimicrobial activity depicted in FIG. 7 and the analytics presented in bar graph 800 provide strong evidence that a singlet oxygen generator core 104 upon irradiation with light (e.g., visible light and/or ultraviolet light) can greatly enhance antimicrobial activity of the star polymer 100 .
- light e.g., visible light and/or ultraviolet light
- the additional antimicrobial activity facilitated by the singlet oxygen generator core 104 can significantly enhance the antimicrobial efficacy (e.g., as evident by the second agar plate 706 , the fourth agar plate 712 , the sixth agar plate 718 , the eighth agar plate 724 , the second bar 804 , the fourth bar 808 , the sixth bar 812 , and the eighth bar 816 ).
- the presence of polymeric chains around the singlet oxygen generator core 104 can extend the circulation time and minimizes toxicity of the otherwise cytotoxic star polymer 100 .
- the star polymer 100 described herein can be used to create a film-forming composition to facilitate surface treatment of various articles such as, but not limited to, food packages and/or medical devices.
- the film-forming composition can comprise a solvent and one or more of the star polymers 100 described herein, wherein the one or more star polymers 100 can be dispersed in the solvent.
- the star polymer 100 can comprise greater than or equal to 0.1 weight percent of the film-forming composition and less than or equal to 50 weight percent of the film-forming composition.
- the star polymer 100 can comprise greater than or equal to 5 weight percent of the film-forming composition and less than or equal to 20 weight percent of the film-forming composition.
- a film-forming composition can comprise a solvent (e.g., water and/or an organic solvent) and a star polymer (e.g., star polymer 100 ).
- the star polymer e.g., star polymer 100
- the star polymer can comprise greater than or equal to 5 weight percent of the film-forming composition and less than or equal to 20 weight percent of the film-forming composition.
- the star polymer e.g., star polymer 100
- the star polymer (e.g., star polymer 100 ) can comprise a singlet oxygen generator core 104 and a plurality of degradable polycarbonate arms 102 .
- the singlet oxygen generator core 104 can be derived from a single oxygen generator molecule (e.g., a porphyrin, a phthalocyanine, a phenothiazine, a xanthene, and/or a quinone). Further, the singlet oxygen generator core 104 can comprise one or more linkage groups (e.g., second linkage group 302 ) to facilitate bonding of the degradable polycarbonate arms 102 . The singlet oxygen generator core 104 can generate one or more singlet oxygen species in response to being irradiated with light (e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm).
- light e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm.
- the plurality of degradable polycarbonate arms 102 can be covalently bonded to the singlet oxygen generator core 104 (e.g., via the second linkage group 302 ).
- the plurality of polycarbonate arms 102 can comprise a cationic functional group 204 covalently bonded to a molecular backbone 202 (e.g., via the first linkage group 208 ).
- the cationic functional group 204 can comprise a nitrogen cation (e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation) and/or a phosphorus cation (e.g., a protonated primary phosphine cation, a protonated secondary phosphine cation, a protonated tertiary phosphine cation, a quaternary phosphonium cation).
- a nitrogen cation e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation
- the cationic functional group 204 can comprise a hydrophobic group (e.g., bonded to the cation).
- the polycarbonate arms 102 can comprise a reactive end group 206 to facilitate a crosslinkage between the star polymer (e.g., star polymer 100 ) and another star polymer (e.g., another star polymer 100 ).
- the film-forming composition can be toxic to a pathogen (e.g., a Gram-negative bacteria, a Gram-positive bacteria, fungi, and/or yeast).
- the film-forming composition can additionally comprise one or more additives to increase efficacy.
- additives can include, but are not limited to: an antimicrobial metal (e.g., nanoparticles of silver, gold, and/or copper), ceramic nanoparticles (e.g., titanium dioxide and/or zinc oxide), antimicrobial metal salts, a pigment, a surfactant, a thickener, an accelerator to speed crosslinking between star polymers 100 , a combination thereof, and/or the like.
- an antimicrobial metal e.g., nanoparticles of silver, gold, and/or copper
- ceramic nanoparticles e.g., titanium dioxide and/or zinc oxide
- antimicrobial metal salts e.g., a pigment, a surfactant, a thickener, an accelerator to speed crosslinking between star polymers 100 , a combination thereof, and/or the like.
- the star polymers 100 do not readily crosslink with other star polymers (e.g., other star polymers 100 ) in the presence of the solvent; rather, said crosslinking is performed upon removal of the solvent.
- the film-forming composition can exhibit a stable shelf life.
- Example solvents include, but are not limited to: water, an organic solvent, a combination thereof, and/or the like.
- FIG. 9 illustrates a flow diagram of an example, non-limiting method 900 for forming a surface treated article. Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity.
- Example articles that can be treated via method 900 include, but are not limited to: food packaging, medical devices, floor surfaces, furniture surfaces, wound care instruments (e.g., bandages and/or gauss), building surfaces, plants (e.g., agricultural crops), ground surfaces, farming equipment, beds, sheets, clothes, blankets, shoes, doors, door frames, walls, ceilings, mattresses, light fixtures, facets, switches, sinks, grab rails, remote controls, vanities, computer equipment, carts, trolleys, hampers, bins, a combination thereof, and/or the like.
- wound care instruments e.g., bandages and/or gauss
- building surfaces e.g., agricultural crops
- ground surfaces farming equipment
- the method 900 can comprise disposing on a surface of an article the film-forming composition described herein.
- the film-forming composition can comprise the star polymer 100 dispersed within a solvent.
- the star polymer 100 can comprise greater than or equal to 5 weight percent of the film-forming composition and less than or equal to 20 weight percent of the film-forming composition.
- the star polymer 100 can comprise a core having a singlet oxygen generator (e.g., singlet oxygen generator core 104 ) and that can generate a singlet oxygen species upon irradiation with light.
- the star polymer 100 can comprise a plurality of polycarbonate arms (e.g., arm 102 ) covalently bonded to the core (e.g., singlet oxygen generator core 104 ).
- the plurality of polycarbonate arms (e.g., arm 102 ) can be degradable and comprise a cation (e.g., cationic functional group 204 ).
- the plurality of polycarbonate arms (e.g., arm 102 ) can have antimicrobial functionality.
- the film-forming composition can be disposed on the surface via a variety of techniques including, but not limited to: dipping, spraying, spin coating, brushing, a combination thereof, and/or the like.
- disposing the film-forming composition coats the surface of the article with an initial layer of star polymers 100 that are not crosslinked to other star polymers (e.g., other star polymers 100 ).
- the method 900 can comprise removing the solvent from the film-forming composition, and thereby, the surface of the coated article.
- the solvent can be removed via evaporation (e.g., by ambient conditions and/or a drying treatment, such as heated air).
- the star polymers 100 left residing on the surface of the article can begin to crosslink with each other, thereby forming a crosslinked film layer on the surface of the article.
- the method 900 can optionally include a thermal and/or photochemical treatment of the surface to facilitate crosslinking between star polymers 100 .
- the thickness of the crosslinked film layer of the star polymers 100 on the surface of the treated article can vary depending on the concentration of the film-forming composition and/or the dispersing technique.
- the method 900 can form a crosslinked layer having a thickness substantially equivalent to one star polymer 100 .
- the method 900 can form a crosslinked layer having a thickness substantially equivalent to a plurality of star polymers 100 .
- the crosslinked film layer can exhibit an opacity greater than or equal to 0% and less than or equal to 100%, with any suitable light absorbing and/or light transmission properties.
- the crosslinked film layer can be any hue, including, but not limited to, red, yellow, blue or combinations thereof.
- the crosslinked film formed by the method 900 can adhere to a variety of surface materials including, but not limited to: metal surfaces, glass surfaces, plastic surfaces, ceramic surfaces, wood surfaces, stone surfaces, textile surfaces, paper surfaces, cloth surfaces, concrete surfaces, synthetic fiber surfaces, organic fiber surfaces, a combination thereof, and/or the like.
- the crosslinked film layer can be treated with one or more chemical agents (e.g., alkylating agents) to increase the antimicrobial effect of the crosslinked film layer.
- biocompatible forms of the star polymer 100 can be utilized with method 900 to form biocompatible crosslinked films that can surface treat insertable medical devices.
- the treated surface comprising the crosslinked film layer can be irradiated with light to facilitate on-demand enhanced antimicrobial functionality.
- the singlet oxygen generator core 104 can generate one or more singlet oxygen species in response to the light.
- the crosslinked film layer can be recovered from the article's surface so as to recycle the star polymer 100 .
- a method 900 of forming a surface treated article can comprise disposing (e.g., at 902 ) on a surface of an article a film-forming composition.
- the film-forming composition can comprise a solvent (e.g., water and/or an organic solvent) and a star polymer (e.g., star polymer 100 ).
- the star polymer e.g., star polymer 100
- the star polymer can comprise a singlet oxygen generator core 104 and a plurality of degradable polycarbonate arms 102 .
- the singlet oxygen generator core 104 can be derived from a single oxygen generator molecule (e.g., a porphyrin, a phthalocyanine, a phenothiazine, a xanthene, and/or a quinone). Further, the singlet oxygen generator core 104 can comprise one or more linkage groups (e.g., second linkage group 302 ) to facilitate bonding of the degradable polycarbonate arms 102 . The singlet oxygen generator core 104 can generate one or more singlet oxygen species in response to being irradiated with light (e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm).
- light e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm.
- the plurality of degradable polycarbonate arms 102 can be covalently bonded to the singlet oxygen generator core 104 (e.g., via the second linkage group 302 ).
- the plurality of polycarbonate arms 102 can comprise a cationic functional group 204 covalently bonded to a molecular backbone 202 (e.g., via the first linkage group 208 ).
- the cationic functional group 204 can comprise a nitrogen cation (e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation) and/or a phosphorus cation (e.g., a protonated primary phosphine cation, a protonated secondary phosphine cation, a protonated tertiary phosphine cation, a quaternary phosphonium cation).
- a nitrogen cation e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation
- the cationic functional group 204 can comprise a hydrophobic group (e.g., bonded to the cation).
- the polycarbonate arms 102 can comprise a reactive end group 206 to facilitate a crosslinking between the star polymer (e.g., star polymer 100 ) and another star polymer (e.g., another star polymer 100 ).
- the film-forming composition can be toxic to a pathogen (e.g., a Gram-negative bacteria, a Gram-positive bacteria, fungi, and/or yeast).
- the method 900 can comprise removing the solvent (e.g., at 904 ) from the surface of the article, and optionally applying a treatment (e.g., at 906 ) to the film-forming composition (e.g., a thermal treatment and/or a photochemical treatment).
- a treatment e.g., at 906
- the film-forming composition e.g., a thermal treatment and/or a photochemical treatment
- the method 1000 can comprise contacting a pathogen with a polymer (e.g., one or more of the star polymers 100 and/or a crosslinked film formed on the surface of an article in accordance to method 900 ).
- a polymer e.g., one or more of the star polymers 100 and/or a crosslinked film formed on the surface of an article in accordance to method 900 .
- the polymer e.g., a star polymer 100
- the polymer can comprise a core having a singlet oxygen generator (e.g., singlet oxygen generator core 104 ) and that can generate a singlet oxygen species upon irradiation with light.
- the polymer e.g., star polymer 100
- the polymer can comprise a plurality of polycarbonate arms (e.g., arm 102 ) covalently bonded to the core (e.g., singlet oxygen generator core 104 ).
- the plurality of polycarbonate arms e.g., arm 102
- the plurality of polycarbonate arms can be degradable and comprise a cation (e.g., cationic functional group 204 ).
- the plurality of polycarbonate arms e.g., arm 102
- the star polymer 100 upon contact, can disrupt a membrane of the pathogen (e.g., via electrostatic disruption and/or hydrophobic integration).
- the one or more star polymers 100 can be located on the surface of an article, whereupon the contacting can comprise a physical meeting of the article's treated surface with the pathogen.
- the pathogen can be located on the surface of an article, whereupon the contacting can comprise a physical meeting of the one or more star polymers 100 with the pathogen.
- the pathogen can be located on an article and the contacting at 1002 can comprise coating the contaminated article with the film-forming composition described herein.
- the pathogen can be located on a crop, wherein the contaminated crop can be sprayed with a film-forming composition comprising the star polymer 100 .
- the method 1000 can further comprise irradiating one or more of the star polymers 100 in contact with the pathogen with light.
- the light can have a wavelength greater than or equal to 10 nanometers and less than or equal to 750 nanometers.
- the one or more star polymers 100 irradiated with light can respond by generating a singlet oxygen species (e.g., via the singlet oxygen generator core 104 ), wherein the singlet oxygen species can facilitate degradation of the pathogen.
- the antimicrobial effects of method 1000 , and thereby the star polymer can be increased on demand via controlled irradiation of the one or more star polymers with light.
- the singlet oxygen generator core 104 can comprise one or more linkage groups (e.g., second linkage group 302 ) to facilitate bonding of the degradable polycarbonate arms 102 .
- the singlet oxygen generator core 104 can generate one or more singlet oxygen species in response to being irradiated with light (e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm).
- the plurality of degradable polycarbonate arms 102 e.g., four polycarbonate arms 102
- the plurality of polycarbonate arms 102 can comprise a cationic functional group 204 covalently bonded to a molecular backbone 202 (e.g., via the first linkage group 208 ).
- the cationic functional group 204 can comprise a nitrogen cation (e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation) and/or a phosphorus cation (e.g., a protonated primary phosphine cation, a protonated secondary phosphine cation, a protonated tertiary phosphine cation, a quaternary phosphonium cation).
- nitrogen cation e.g., a protonated primary amine cation, a protonated secondary amine
- the cationic functional group 204 can comprise a hydrophobic group (e.g., bonded to the cation).
- the polycarbonate arms 102 can comprise a reactive end group 206 to facilitate a crosslinkage between the star polymer (e.g., star polymer 100 ) and another star polymer (e.g., another star polymer 100 ).
- the polymer e.g., star polymer 100
- the method 1000 can further comprise irradiating the polymer with the light (e.g., at 1004 ), thereby generating the singlet oxygen species via the singlet oxygen generator core 104 within the star polymer.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Plant Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Inorganic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Polyesters Or Polycarbonates (AREA)
- Materials For Medical Uses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
- The subject disclosure relates to a star polymer with antimicrobial activity, and more specifically, to a star polymer that can exhibit enhanced antimicrobial activity in response to light.
- The following presents a summary to provide a basic understanding of one or more embodiments of the invention. This summary is not intended to identify key or critical elements, or delineate any scope of the particular embodiments or any scope of the claims. Its sole purpose is to present concepts in a simplified form as a prelude to the more detailed description that is presented later. In one or more embodiments described herein, compositions and methods regarding star polymers that can exhibit enhanced antimicrobial activity in response to light are described.
- According to an embodiment, a polymer is provided. The polymer can comprise a core that can have a singlet oxygen generator and that can generate a singlet oxygen species upon irradiation with light. The polymer can further comprise a plurality of polycarbonate arms covalently bonded to the core. The plurality of polycarbonate arms can be degradable and can comprise a cation. Further, the plurality of polycarbonate arms can have antimicrobial functionality.
- According to another embodiment, a method is provided. The method can comprise forming a plurality of degradable polycarbonate arms by polymerizing a plurality of carbonates with a singlet oxygen generator core. The singlet oxygen generator core can generate a singlet oxygen species in response to being irradiated with light. The method can also comprise generating a cationic moiety by covalently bonding a functional group with a degradable polycarbonate arm from the plurality of degradable polycarbonate arms.
- According to another embodiment, a film-forming composition is provided. The film-forming composition can comprise a solvent and a polymer. The polymer can comprise greater than or equal to 5 weight percent of the film-forming composition and less than or equal to 20 weight percent of the film-forming composition. Further, the polymer can be dispersed in the solvent. The polymer can also comprise a core that can have a singlet oxygen generator and that can generate a singlet oxygen species upon irradiation with light. The polymer can further comprise a plurality of polycarbonate arms covalently bonded to the core. The plurality of polycarbonate arms can be degradable and can comprise a cation. Moreover, the plurality of polycarbonate arms can have antimicrobial functionality.
- According to another embodiment, a method of forming a surface treated article is provided. The method can comprise disposing on a surface of an article a film-forming composition. The film-forming composition can comprise a solvent and a polymer. The polymer can comprise greater than or equal to 5 weight percent of the film-forming composition and less than or equal to 20 weight percent of the film-forming composition. Further, the polymer can be dispersed in the solvent. The polymer can also comprise a core that can have a singlet oxygen generator and that can generate a singlet oxygen species upon irradiation with light. The polymer can further comprise a plurality of polycarbonate arms covalently bonded to the core. The plurality of polycarbonate arms can be degradable and can comprise a cation. Moreover, the plurality of polycarbonate arms can have antimicrobial functionality. The method can additionally comprise removing the solvent from the surface of the article.
- According to another embodiment, a method of killing a pathogen is provided. The method can comprise contacting the pathogen with a polymer. The polymer can comprise a core that can have a singlet oxygen generator and that can generate a singlet oxygen species upon irradiation with light. The polymer can further comprise a plurality of polycarbonate arms covalently bonded to the core. The plurality of polycarbonate arms can be degradable and can comprise a cation. Further, the plurality of polycarbonate arms can have antimicrobial functionality. Moreover, the contacting of the pathogen with the polymer can electrostatically disrupt a membrane of the pathogen.
-
FIG. 1 illustrates a diagram of an example, non-limiting star polymer in accordance with one or more embodiments described herein. -
FIG. 2 illustrates a diagram of an example, non-limiting arm from a plurality of arms that can comprise a star polymer in accordance with one or more embodiments described herein. -
FIG. 3 illustrates a diagram of an example, non-limiting singlet oxygen generator core that can comprise a star polymer in accordance with one or more embodiments described herein. -
FIG. 4 illustrates a flow diagram of an example, non-limiting method that can facilitate generation of a star polymer in accordance with one or more embodiments described herein. -
FIG. 5 illustrates a diagram of an example, non-limiting scheme that can facilitate generation of a star polymer in accordance with one or more embodiments described herein. -
FIG. 6 illustrates a diagram of an example, non-limiting chart that can demonstrate a composition of a star polymer generated in accordance with one or more embodiments described herein. -
FIG. 7 illustrates four photos of example, non-limiting agar plates that can demonstrate the antimicrobial efficacy of a star polymer in accordance with one or more embodiments described herein. -
FIG. 8 illustrates a diagram of an example, non-limiting bar graph that can demonstrate the antimicrobial efficacy of a star polymer in accordance with one or more embodiments described herein. -
FIG. 9 illustrates another flow diagram of an example, non-limiting method that can facilitate treating a surface of an article with a film-forming composition in accordance with one or more embodiments described herein. -
FIG. 10 illustrates another flow diagram of an example, non-limiting method that can facilitate killing a pathogen through contact with a star polymer in accordance with one or more embodiments described herein. - The following detailed description is merely illustrative and is not intended to limit embodiments and/or application or uses of embodiments. Furthermore, there is no intention to be bound by any expressed or implied information presented in the preceding Background or Summary sections, or in the Detailed Description section.
- One or more embodiments are now described with reference to the drawings, wherein like referenced numerals are used to refer to like elements throughout. In the following description, for purposes of explanation, numerous specific details are set forth in order to provide a more thorough understanding of the one or more embodiments. It is evident, however, in various cases, that the one or more embodiments can be practiced without these specific details.
- In the recent decades, there has been a rise in antibiotic-resistant bacteria. Systemic overuse of broad-spectrum antibiotics has lead to a rise in multi-medication resistant bacteria commonly referred to as “superbugs.” Further, biofilms can form on human tissue and implanted devices, leading to implant failure. The biofilms can be composed of bacteria embedded within a self-produced extracellular polymeric matrix. Thus, the biofilms can be difficult to penetrate, thereby rendering it difficult to kill the embedded bacteria.
- As an alternative to conventional antibiotic techniques, reactive oxygen species (ROS) can exhibit strong antimicrobial, antiviral, and antifungal activity. Multiple reports claim that ROS can have high efficacy against various pathogens such as, but not limited to: Gram-positive bacteria, Gram-negative bacteria, fungi, and yeast. Further, ROS can be effective in cleansing and/or treating stagnate wounds and treating chronic obstructive pulmonary disease. Unfortunately, while ROS can be toxic to various pathogens, they can be equally as toxic against host cells. Additionally, conventional ROS can be unstable and exhibit undesirable burst releases.
- Various embodiments described herein can provide compositions (e.g., film-forming compositions) and/or methods for the synthesis and/or use of antimicrobial star polymers with enhanced activity provided by light activated singlet oxygen generating functionalities. As used herein, the term “star polymer” can refer to a polymer having a plurality of arms, which can be crosslinked, branching from a discrete core. One or more embodiments can regard a polymer that can comprise a plurality of positively charged degradable polycarbonate arms covalently bonded to a singlet oxygen generating polymer core. In various embodiments, a film-forming composition can comprise the polymer compositions described herein. Further, one or embodiments can regard methods utilizing the polymer composition and/or film-forming composition to kill, and/or prevent contamination and/or growth of, various pathogens (e.g., Gram-positive bacteria, Gram-negative bacteria, fungi, and yeast) and/or surface treat various articles (e.g., food and/or medical packaging).
-
FIG. 1 illustrates a diagram of an example,non-limiting star polymer 100 in accordance with one or more embodiments described herein. Thestar polymer 100 can comprise a plurality ofpolycarbonate arms 102 covalently bonded to a singletoxygen generator core 104. In various embodiments, thestar polymer 100 can crosslink with one or more additional star polymers (e.g., star polymer 100) without the assistance of an additional chemical crosslinking agent and/or photochemical activation. The crosslinking can be chemical (e.g., covalent bonds), physical (e.g., hydrophobic bonding, chain entanglement, and/or ionic association), and/or a combination thereof. The plurality ofpolycarbonate arms 102 can be present in thestar polymer 100 as homopolymers, random copolymers, block polymers, and/or a combination thereof. - In various embodiments, the
star polymer 100 can comprise one or more functionalization sites that can be utilized to control chemical interactions that can facilitate antimicrobial and/or film-forming properties. For example, plurality of thepolycarbonate arms 102 and/or the singletoxygen generator core 104 can be capable of further chain growth. -
FIG. 2 illustrates a drawing of an example,non-limiting polycarbonate arm 102 of the plurality ofpolycarbonate arms 102 that can comprise thestar polymer 100. Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity. In various embodiments, eachpolycarbonate arm 102 from the plurality ofpolycarbonate arms 102 can be characterized by the same structure. In one or more embodiments, one ormore polycarbonate arms 102 of thestar polymer 100 can exhibit the features described herein via a chemical structure different than one or moreother polycarbonate arms 102 of thestar polymer 100. Further, in some embodiments, the plurality ofpolycarbonate arms 102 can comprise fourpolycarbonate arms 102. - The
polycarbonate arm 102 can have a positive charge when bonded to the singletoxygen generator core 104. Thepolycarbonate arm 102 can comprise amolecular backbone 202 covalently bonded to the singletoxygen generator core 104. Also, thepolycarbonate arm 102 can comprise a cationicfunctional group 204 covalently bonded to themolecular backbone 202. In one or more embodiments, thepolycarbonate arm 102 can further comprise areactive end group 206 covalently bonded to themolecular backbone 202. - As shown in
FIG. 2 , “X” can represent the singletoxygen generator core 104. Thus,FIG. 2 delineates that the polycarbonate arm's 102molecular backbone 202 can be bonded to the singletoxygen generator core 104.FIG. 2 illustrates an exemplary structure; however, alternate structures are also envisaged. Example chemical structures comprising themolecular backbone 202 can include, but are not limited to: alkyl structures, aryl structures, alkane structures, aldehyde structures, ether structures, ketone structures, ester structures, carboxyl structures, carbonyl structures, amine structures, amide structures, phosphide structures, phosphine structures, a combination thereof, and/or the like. One of ordinary skill in the art can recognize that the size of themolecular backbone 202 can vary depending of the desired function of thestar polymer 100. For example, “n” can represent an integer great than or equal to 5 and less than or equal to 1000. - Additionally, the
molecular backbone 202 can be covalently bonded to the cationic functional group 204 (e.g., illustrated inFIG. 2 as “R”). In one or more embodiments, the cationicfunctional group 204 can be bonded to themolecular backbone 202 via afirst linkage group 208.FIG. 2 illustrates thefirst linkage group 208 having an ester structure; however other chemical structures are also envisaged. Example chemical structures for thefirst linkage group 208 can include, but are not limited to: alkyl structures, aryl structures, alkane structures, ether structures, carboxyl structures, ketone structures, ester structures, carboxyl structures, carbonyl structures, a combination thereof, and/or the like. In one or more embodiments, thefirst linkage group 208 can be a product of polymerization used to form thepolycarbonate arm 102. In some embodiments, thefirst linkage group 208 can be a product of post-polymerization of thepolycarbonate arm 102. - The cationic
functional group 204 can comprise one or more nitrogen and/or phosphorus cations. Example nitrogen cations can include, but are not limited to: quaternary ammonium cations, protonated primary amine cations, protonated secondary amine cations, protonated tertiary amine cations, and/or imidazolium cations. Example, phosphorus cations can include, but are not limited to: quaternary phosphonium cations, protonated primary phosphine cations, protonated secondary phosphine cations, and/or protonated tertiary cations. Additionally, the cationicfunctional group 204 can comprise a hydrophobic group (e.g., an alkyl group and/or an aryl group) bonded to the one or more nitrogen cations and/or phosphorus cations. The nitrogen cations and/or phosphorus cations can be formed via protonation, alkylation, and/or quaternization. - In various embodiments, the
polycarbonate arm 102 can further comprise areactive end group 206 bonded to themolecular backbone 202. Thereactive end group 206 can facilitate self-crosslinking of thestar polymer 100 with another star polymer (e.g., another star polymer 100). Thereactive end group 206 can comprise a halide ion located alpha to a carbonyl group and/or alpha to an aromatic ring. Example, halide ions include: fluoride, chloride, bromide, iodide, and astatide. Example carbonyl groups include, but are not limited to: alpha-halo ketones, alpha-halo esters, alpha-halo acids, alpha-halo amides, and/or a combination thereof. Example aromatic rings include, but are not limited to: phenyl, pyridinyl, and/or the like. - In various embodiments, the
reactive end group 206 can be a product of polymerization used to form thepolycarbonate arm 102. For example, thereactive end group 206 can comprise: an epoxide (e.g., from anionic polymerization), an alkoxyamine (e.g., from controlled radical polymerization), a dithioester (e.g., from reversible addition-fragmentation transfer polymerization), and/or a trithiocarbonate (e.g., from reversible addition-fragmentation transfer polymerization). In one or more embodiments, thereactive end group 206 can be prepared by chemically modifying the peripheral end of thepolycarbonate arm 102. For example, the peripheral end of thepolycarbonate arm 102 can be modified to produce areactive end group 206 including, but not limited to: an azide, a thiol, an olefin, and/or an aryl substituted ketone. - Thus, in various embodiments, the
polycarbonate arm 102 can be a degradable polycarbonate covalently bonded to a discrete singletoxygen generator core 104, and thepolycarbonate arm 102 can comprise amolecular backbone 202 bonded to a cationicfunctional group 204. The cationicfunctional group 204 can be positively charged (e.g., via one or more nitrogen and/or phosphorus cation) to facilitate antimicrobial functionality. Additionally, the cationicfunctional group 204 can comprise a hydrophobic group (e.g., bonded to the to one or more nitrogen and/or phosphorus cations), which can further enhance antimicrobial functionality. The cationicfunctional group 204 can be directly bonded to themolecular backbone 202, and/or the cationicfunctional group 204 can be bonded to themolecular backbone 202 via a first linkage group 208 (e.g., thefirst linkage group 208 can be formed as a product of the polymerization of the polycarbonate arm 102). Moreover, themolecular backbone 202 can be bonded to areactive end group 206, which can facilitate crosslinkage of thestar polymer 100 with another star polymer (e.g., star polymer 100). - The plurality of
polycarbonate arms 102 can exhibit antimicrobial functionality through a lysis of pathogen cells. For example, a membrane of a subject pathogen cell can comprise a phospholipid bilayer. The phospholipid bilayer can comprise a plurality of molecules having hydrophilic heads and/or hydrophobic tails. Additionally, one or more of the plurality of membrane molecules can be negatively charged. The positive charge of the polycarbonate arm 102 (e.g., via the cationic functional group 204) can attract thestar polymer 100 to the negatively charged membrane molecules and facilitate cleaving of said molecules from adjacent membrane molecules. The hydrophobicity of the polycarbonate arm 102 (e.g., via the cationic functional group 204) can further facilitate said cleaving as the hydrophobic group of the cationicfunctional group 204 integrates itself into the hydrophobic region of the membrane. Thus, thepolycarbonate arm 102 can facilitate a lysis of the pathogen cell through electrostatic disruption and/or hydrophobic membrane integration. Example pathogen cells that can be subject to the antimicrobial effects of thepolycarbonate arm 102 can include, but are not limited to: Gram-negative bacteria, Gram-positive bacteria, fungi and yeast. -
FIG. 3 illustrates a diagram of an example, non-limiting singletoxygen generator core 104 that can comprise thestar polymer 100. Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity. In one or more embodiments, the plurality ofpolycarbonate arms 102 can be crosslinked together and/or covalently bonded to the singletoxygen generator core 104. -
FIG. 3 shows the singletoxygen generator core 104 with an exemplary chemical structure derived from a porphyrin; however, other chemical structures are also envisaged. For example, the singletoxygen generator core 104 can have a chemical structure derived from a molecule selected from a group that can include, but is not limited to: a phthalocyanine, a phenothiazine, a xanthene, and/or a quinone. The singletoxygen generator core 104 can comprise one or more second linkage groups 302 (e.g., represented by “L” inFIG. 3 ) that can facilitate bonding the plurality of polycarbonate arms 102 (e.g., represented by “A” inFIG. 3 ) to the singletoxygen generator core 104. For example, thesecond linkage group 302 can be derived from an alcohol and/or an ether (e.g., an alcohol comprising a halide). In one or more embodiments, a periphery of thesecond linkage group 302 can comprise an oxygen atom (e.g., derived from a hydroxyl group) such that a polycarbonate structure is formed by the bonding of anarm 102 and asecond linkage group 302. - Upon being irradiated with light, the singlet
oxygen generator core 104 can generate one or more singlet oxygen species, which can enhance antimicrobial functionality of thestar polymer 100. Thus, thestar polymer 100 can exhibit enhanced anti-microbial functionality on-demand. For example, the singletoxygen generator core 104 can generate one or more singlet oxygen species in response to light having a wavelength greater than or equal to 10 nanometers (nm) and less than or equal to 750 nm. -
FIG. 4 illustrates a flow diagram of an example,non-limiting method 400 that can facilitate generating thestar polymer 100 in accordance with in one or more embodiments described herein. Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity. - At 402, the
method 400 can comprise preparing the singletoxygen generator core 104 by polymerizing a singlet oxygen generator molecule with a first functional group. For example, the singlet oxygen generator molecule and the first functional group can be mixed together in a solvent to form a solution. The solution can then be heated (e.g., to a temperature greater than or equal to 100 degrees Celsius (° C.) and less than or equal to 200° C.). Further, the solution can be agitated (e.g., stirred) for a defined period of time (e.g., greater than or equal to 12 hours and less than or equal to 48 hours). Also, the solution can optionally be agitated under nitrogen gas. The singletoxygen generator core 104 can form as a precipitate of the solution. - Preparing the singlet
oxygen generator core 104 can comprise bonding one or more first functional groups to a singlet oxygen generating molecule. The singlet oxygen generating molecule can generate one or more singlet oxygen species in response to being irradiated with light (e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm). Example singlet oxygen generating molecules can include, but are not limited to: a porphyrin, a phthalocyanine, a phenothiazine, a xanthene, a quinone, and/or the like. Example first functional groups can comprise alcohol groups, carboxyl groups, ester groups, and/or one or more halides. Further, the one or more first functional groups can facilitate a bonding of the plurality ofpolycarbonate arms 102 to the singlet oxygen generating molecule and later become thesecond linkage group 302 when said bonding occurs. For example, one or more first functional groups can comprise an alcohol group such that the preparing at 402 results in a singletoxygen generator core 104 comprising one or more hydroxyl groups that can facilitate the polymerization of a plurality ofpolycarbonate arms 102. - At 404, the
method 400 can comprise forming a plurality ofdegradable polycarbonate arms 102 by polymerizing a plurality of carbonates with the prepared singlet oxygen generator core 104 (e.g., in the presence of an organocatylst). For example, the plurality of carbonates and the prepared singletoxygen generator core 104 can be mixed with one or more solvents and/or one or more organocatylsts to form a solution. The solution can be agitated (e.g., stirred) at room temperature (“RT”) for a defined period of time (e.g., greater than or equal to 30 minutes and less than or equal to 120 minutes). - The polymerization at 404 can covalently bond a plurality of carbonates together to form a one or more degradable polycarbonate structures, and/or the polymerization can covalently bond the one or more degradable polycarbonate structures to the prepared singlet
oxygen generator core 104. Further, one or more of the carbonates and/or one or more of the polycarbonate structures can comprise a second functional group. The second functional group can facilitate later generation of the cationicfunctional group 204. For example, the second functional group can comprise an alkyl halide. - Covalently bonding the plurality of carbonates together to form the polycarbonate structure can form the
molecular backbone 202. Further, one or more of the polycarbonate structures can be covalently bonded to the first functional group to facilitate bonding to the prepared singletoxygen generator core 104, whereupon the first functional group can become thesecond linkage group 302. - For example, the one or more of the plurality of carbonates can be cyclic carbonates, and the polymerization at 404 can comprise ring-opening polymerization (ROP) of the cyclic carbonates to form a polycarbonate structure (e.g., molecular backbone 202). The one or more carbonates can have a structure characterized by formula 1:
- wherein R1 can represent the second functional group. Thus, the ROP can form a polycarbonate structure characterized by formula 2:
- wherein R1 can represent the second functional group, “X” can represent a bond to the singlet oxygen generator core 104, and “n” can represent an integer greater than or equal to 5 and less than or equal to 1000. For instance, the second functional group can be 4-methylbenzyl chloride, thereby rendering one or more carbonates of 2-oxo-5-methyl-1,3-dioxane-5-carboxylic acid 4-(chloromethyl)benzyl ester (“MTC-OBnCl”). Whereupon, the polymerization at 404 can comprise a ROP of the MTC-OBnCl carbonates to form a polycarbonate structure characterized by formula 3:
- wherein “X” can represent a bond to the singlet
oxygen generator core 104, and “n” can represent an integer greater than or equal to 5 and less than or equal to 1000. In the examples described above, thefirst linkage group 208 is formed as a result of the polymerization at 404; however, as described herein, thefirst linkage group 208 can also be formed post said polymerization at 404. Similarly, in one or more embodiments, the second functional group can be covalently bonded to one or more of the carbonates prior to the polymerization at 404; while in some embodiments the second functional group can be covalently bonded to the polycarbonate structure post polymerization at 404. - At 406, the
method 400 can comprise generating a cationic moiety (e.g. the cationic functional group 204) by covalently bonding a third functional group with adegradable polycarbonate arm 102 from the plurality of degradable polycarbonate arms 102 (e.g., polycarbonate structures that can be characterized by molecular backbone 202), thereby forming thestar polymer 100. For example, the intermediate structure formed at 404 can be mixed with the third functional group in a solvent at RT for a defined period of time (e.g., greater than or equal to one day and less than or equal to three days). Also, the solvent can comprise an acetyl group. - The third functional group can comprise an amine group, an imidazole (e.g., a structure comprising an imidazole ring) and/or a phosphine group. Further, generating the cationic moiety (e.g., cationic functional group 204) at 406 can comprise covalently bonding the third functional group to a second functional group of a polycarbonate structure formed at 404. For example, the third functional group can be covalently bonded to the second functional group through alkylation and/or quaternization. The third functional group can be covalently bonded to the second functional group in the presence of an acetyl group to generate the cationic moiety (e.g., the cationic functional group 204).
- Thus, in various embodiments, the
method 400 can comprise preparing (e.g., at 402) a singletoxygen generator core 104 by polymerizing a singlet oxygen generator molecule (e.g., a porphyrin, a phthalocyanine, a phenothiazine, a xanthene, and/or a quinone) with one or more first functional groups (e.g., an alcohol group). The singletoxygen generator core 104 can generate a singlet oxygen species in response to light (e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm). Also, themethod 400 can comprise forming (e.g., at 404) a plurality of degradable polycarbonate structures (e.g., characterized by molecular backbone 202) by polymerizing a plurality of carbonates with the singlet oxygen generator core 104 (e.g., in the presence of an organocatalyst). The polymerization can covalently bond the plurality of carbonates together to form the one or more polycarbonate structures (e.g., characterized by themolecular backbone 202 of a plurality of degradable polycarbonate arms 102). The polymerization can also form one or more second functional groups bonded to the one or more polycarbonate structures, wherein the second functional groups (e.g., an alkyl halide) can facilitate generation of one or more cationic moieties. Further, the polymerization can covalently bond the one or more polycarbonate structures to the singletoxygen generator core 104 via the first functional group, whereupon the first functional group can thereby transform into a linkage group (e.g., second linkage group 302). Additionally, themethod 400 can comprise generating (e.g., at 406) one or more cation moieties (e.g., cationic functional group 204) by covalently bonding one or more third functional groups (e.g., an amine group, an imidazole group, and/or a phosphine group) with one or more of the polycarbonate structures to form a plurality of positively charged degradable polycarbonates (e.g., polycarbonate arms 102), and thereby a star polymer (e.g., star polymer 100). Generating the one or more cationic moieties can comprise an alkylation and/or quaternization of the third functional group with the second functional group to generate the one or more cationic moieties (e.g., cation functional group 204), whereupon the second functional group can thereby transform into another linkage group (e.g., first linkage group 208). The one or more cationic moieties can comprise a nitrogen cation (e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation) and/or a phosphorus cation (e.g., a protonated primary phosphine cation, a protonated secondary phosphine cation, a protonated tertiary phosphine cation, a quaternary phosphonium cation). Moreover, the one or more of the generated cation moieties can further comprise a hydrophobic functional group (e.g., bonded to the nitrogen cation and/or the phosphorus cation). In addition, the polymerized degradable polycarbonates (e.g., polycarbonate arms 102) can comprise a reactive functional group (e.g., reactive end group 206) to facilitate crosslinkage of the star polymer (e.g., star polymer 100) with another star polymer (e.g., another star polymer 100). -
FIG. 5 illustrates a diagram of an example,non-limiting scheme 500 that can exemplify the formation of astar polymer 100 in accordance with one or more embodiments described herein (e.g., method 400). Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity. - At 502, the
scheme 500 can depict a preparation of the singlet oxygen generator core 104 (e.g., in accordance with 402 of method 400). For example, 5,10,15,20-Tetrakis(4hydroxyphenyl)porphyrin (“TPP”) can be polymerized with 2-bromoethanol in potassium carbonate and dimethylformamide (“DMF”) to produce hydroxyl-TPP. Here, the ethanol can serve as the first functional group, thereby providing a hydroxyl group to facilitate covalent bonding of one or more polycarbonate structures (e.g., molecular backbone 202). - At 504, the
scheme 500 can depict forming the plurality of degradable polycarbonate structures (e.g., characterized by molecular backbone 202) by polymerizing a plurality of carbonates with the singletoxygen generator core 104 in an organocatlyst (e.g., in accordance with 404 of method 400). For example, the hydroxyl-TPP can be polymerized with a plurality of MTC-OBnCl carbonates in the presence of dichloromethane (“DCM”), 1,8-diazabicyclo[5.4.0]undec-7-ene (“DBU”), and 1-1-[3,5-bis(trifluoromethyl)-phenyl]-3-cyclohexyl-2-thiourea (“TU”) for defined period of time (e.g., two hours). As the plurality of carbonates polymerize together, they can form one or moremolecular backbones 202. Also, as the polycarbonate structures polymerize, they can covalently bond to one or more of the hydroxyl groups of the hydroxyl-TPP; thereby transforming the one or more first functional groups into the one or moresecond linkage groups 302. Further, the 4-methylbenzyl chloride functional group of the carbonates can serve as the second functional group, which can facilitate generating the cationic moiety. As depicted inFIG. 5 , the polymerization at 504 can produce an intermediate structure in thescheme 500. - At 506, the
scheme 500 can depict a generation of one or more cationic moieties (e.g., cationic functional group 204) by covalently bonding one or more third functional groups with one or more of the degradable polycarbonate structures (e.g., in accordance with 406 of method 400). For example, the intermediate structure can be mixed with dimethylbutylamine in acetonitrile (“AcCN”) to form a solution. The solution can be agitated (e.g., stirred) at RT for a defined period of time (e.g., greater than or equal to 1 hour and less than or equal to 6 hours). Here, the dimethylbutylamine can serve as the third functional group, and quaternization of the dimethylbutylamine can bond the dimethylbutylamine to the second functional group and form a nitrogen cation (e.g., a quaternary ammonium cation), thereby installing a positive charge to the plurality ofpolycarbonate arms 102. Subsequently, the solvent can be removed from the solution and a dialysis can be performed to retrieve the product (e.g., the star polymer 100). For example, the dialysis can be carried out over a defined period of time (e.g., greater than or equal to one day and less than or equal to three days) at RT using 1:1 alcohol and acetonitrile. -
FIG. 6 illustrates a diagram of an example,non-limiting chart 600 that can confirm the structure of astar polymer 100 created byscheme 500 in accordance with one or more embodiments described herein (e.g., method 400). Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity. - In one or more embodiments, a
star polymer 100 can be generated in accordance withmethod 400 and/orscheme 500. For example, 200 milligrams (mg) of 0.029 millimole (mmol) TPP can be charged in a 50 milliliter (mL) flask equipped with a stir bar with 501 mg of 3.63 mmol potassium carbonate and 8.61 microliters (μL) of 0.044 mmol 15-crown-5 in 25 mL of DMF. The reaction mixture can be stirred for 15 minutes at RT before 185 μL of 2.61 mmol 2-bromoethanol can be added in a dropwise fashion. Subsequently, the mixture can be heated at 140° C. and stirred under nitrogen for 24 hours. After the reaction has proceeded completely, the solvent can be removed under vacuum and the residual solids can be dissolved in 25 mL of tetrahydrofuran (“THF”). An organic layer can then be extracted twice with 15 mL of water, once with 15 mL of brine, and dried over sodium sulfate. Subsequently, the solvent can be removed and the crude product can be re-dissolved in 5 mL of THF. Next, a precipitation in cold diethyl ether can follow. The precipitate can be filtered and placed under vacuum for 18 hours, whereupon the final product can be hydroxyl-TPP. - Further, 4.3 mg of 0.005 mmol hydroxyl-TPP and 150 mg of 0.5 mmol MTC-OBnCl can be placed in a 20 mL glass vial equipped with a stir bar. Additionally, DCM can be added to the glass vial to ensure all solids are dissolved. The monomer concentration can be calibrated to 2 moles per liter (M). After which, 3.7 μL of 0.025 mmol DBU and 9.3 mg of 0.025 mmol TU can be added to initiate polymerization. The mixture can be stirred at RT for 1.5 hours. Next, 30 mg of benzoic acid can be added to the mixture to quench the reaction. Subsequently, the polymer intermediate can be purified via precipitation in cold diethyl ether and dried under vacuum.
- The polymer intermediate can then be dissolved in 2 mL of acetonitrile and subsequently, quaternized with 750 μL of dimethylbutylamine at RT with stirring for 4.5 hours. The solvent can be removed under vacuum and the quaternized polymer can be dissolved in 4 mL of isopropanol and acetonitrile mixture having a 1:1 ratio. Further, the solution can be placed within a dialysis bag of 1000 molecular weight cut-off. Dialysis can be carried for two days at RT using 1:1 isopropanol and acetonitrile. Lastly, the solvents can be removed and the polymer lyophilized to obtain a
star polymer 100 product. - The chemical structure of the
star polymer 100 product can then be analyzed using proton nuclear magnetic resonance (1H NMR) to generatechart 600.Chart 600 illustrates that the polymer generated in accordance with one or more embodiments described herein (e.g.,method 400 and/or scheme 500) can exhibit the features of astar polymer 100 described herein. For example, 1H NMR spectra can be recorded on a Bruker Avance 2000 spectrometer operating at 400 mega hertz (MHz) (proton) and can be referenced to an internal solvent (e.g., 1H=7.26 parts per million (ppm)). The 1H NMR spectra can be recorded at RT using standard Bruker library pulse programs. Further, analytical permeation chromatography (GPC) and/or dynamic light scattering (LS) measurements can be conducted. -
FIG. 7 illustrates eight photos of example, non-limiting agar plates used to demonstrate the antimicrobial efficacy of thestar polymer 100. Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity. For example, the eight photos are illustrated in pairs to demonstrate the effect of irradiating thestar polymer 100 with light at varying concentrations. Each of the agar plates shown inFIG. 7 comprise a growth solution, a bacterial culture of Pseudomonas aeruginosa, and a concentration of thestar polymer 100 formed in accordance withmethod 400 and/orscheme 500 and analyzed bychart 600. - The
first photo pair 702 can regard agar plates comprising thestar polymer 100 at a 16 micrograms per milliliter (μg/mL) concentration. Thefirst agar plate 704 can depict the antimicrobial functionality of thestar polymer 100 at 16 μg/mL, wherein thestar polymer 100 is not irradiated with light. Thesecond agar plate 706 can depict the antimicrobial functionality of thestar polymer 100 at 16 μg/mL, wherein thestar polymer 100 is irradiated with light. - The
second photo pair 708 can regard agar plates comprising thestar polymer 100 at a 31 micrograms per milliliter (μg/mL) concentration. Thethird agar plate 710 can depict the antimicrobial functionality of thestar polymer 100 at 31 μg/mL, wherein thestar polymer 100 is not irradiated with light. Thefourth agar plate 712 can depict the antimicrobial functionality of thestar polymer 100 at 31 μg/mL, wherein thestar polymer 100 is irradiated with light. - The
third photo pair 714 can regard agar plates comprising thestar polymer 100 at a 63 micrograms per milliliter (μg/mL) concentration. Thefifth agar plate 716 can depict the antimicrobial functionality of thestar polymer 100 at 63 μg/mL, wherein thestar polymer 100 is not irradiated with light. Thesixth agar plate 718 can depict the antimicrobial functionality of thestar polymer 100 at 63 μg/mL, wherein thestar polymer 100 is irradiated with light. - The
fourth photo pair 720 can regard agar plates comprising thestar polymer 100 at a 125 micrograms per milliliter (μg/mL) concentration. Theseventh agar plate 722 can depict the antimicrobial functionality of thestar polymer 100 at 125 μg/mL, wherein thestar polymer 100 is not irradiated with light. Theeighth agar plate 724 can depict the antimicrobial functionality of thestar polymer 100 at 125 μg/mL, wherein thestar polymer 100 is irradiated with light. -
FIG. 8 illustrates a diagram of an example,non-limiting bar graph 800 that analytically exemplifies the antimicrobial effect of each of the agar plates depicted inFIG. 7 . Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity. Thefirst bar 802 can regard thefirst agar plate 704; thesecond bar 804 can regard thesecond agar plate 706; thethird bar 806 can regard thethird agar plate 710; thefourth bar 808 can regard thefourth agar plate 712; thefifth bar 810 can regard thefifth agar plate 716; thesixth bar 812 can regard thesixth agar plate 718; seventh bar 814 can regard theseventh agar plate 722; and theeighth bar 816 can regard theeighth agar plate 724. - The visual appearance of antimicrobial activity depicted in
FIG. 7 and the analytics presented inbar graph 800 provide strong evidence that a singletoxygen generator core 104 upon irradiation with light (e.g., visible light and/or ultraviolet light) can greatly enhance antimicrobial activity of thestar polymer 100. While the plurality ofpolycarbonate arms 102 exhibit antimicrobial functionality (e.g., as evident by thethird agar plate 710, thefifth agar plate 716, theseventh agar plate 722, thethird bar 806, thefifth bar 810, and the seventh bar 814) independently, the additional antimicrobial activity facilitated by the singletoxygen generator core 104 can significantly enhance the antimicrobial efficacy (e.g., as evident by thesecond agar plate 706, thefourth agar plate 712, thesixth agar plate 718, theeighth agar plate 724, thesecond bar 804, thefourth bar 808, thesixth bar 812, and the eighth bar 816). Moreover, the presence of polymeric chains around the singletoxygen generator core 104 can extend the circulation time and minimizes toxicity of the otherwisecytotoxic star polymer 100. - In various embodiments, the
star polymer 100 described herein can be used to create a film-forming composition to facilitate surface treatment of various articles such as, but not limited to, food packages and/or medical devices. The film-forming composition can comprise a solvent and one or more of thestar polymers 100 described herein, wherein the one ormore star polymers 100 can be dispersed in the solvent. In various embodiments, thestar polymer 100 can comprise greater than or equal to 0.1 weight percent of the film-forming composition and less than or equal to 50 weight percent of the film-forming composition. In some embodiments, thestar polymer 100 can comprise greater than or equal to 5 weight percent of the film-forming composition and less than or equal to 20 weight percent of the film-forming composition. - Thus, in one or more embodiments a film-forming composition can comprise a solvent (e.g., water and/or an organic solvent) and a star polymer (e.g., star polymer 100). The star polymer (e.g., star polymer 100) can comprise greater than or equal to 5 weight percent of the film-forming composition and less than or equal to 20 weight percent of the film-forming composition. The star polymer (e.g., star polymer 100) can be dispersed in the solvent. Also, the star polymer (e.g., star polymer 100) can comprise a singlet
oxygen generator core 104 and a plurality ofdegradable polycarbonate arms 102. The singletoxygen generator core 104 can be derived from a single oxygen generator molecule (e.g., a porphyrin, a phthalocyanine, a phenothiazine, a xanthene, and/or a quinone). Further, the singletoxygen generator core 104 can comprise one or more linkage groups (e.g., second linkage group 302) to facilitate bonding of thedegradable polycarbonate arms 102. The singletoxygen generator core 104 can generate one or more singlet oxygen species in response to being irradiated with light (e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm). The plurality of degradable polycarbonate arms 102 (e.g., four polycarbonate arms 102) can be covalently bonded to the singlet oxygen generator core 104 (e.g., via the second linkage group 302). The plurality ofpolycarbonate arms 102 can comprise a cationicfunctional group 204 covalently bonded to a molecular backbone 202 (e.g., via the first linkage group 208). The cationicfunctional group 204 can comprise a nitrogen cation (e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation) and/or a phosphorus cation (e.g., a protonated primary phosphine cation, a protonated secondary phosphine cation, a protonated tertiary phosphine cation, a quaternary phosphonium cation). Further, the cationicfunctional group 204 can comprise a hydrophobic group (e.g., bonded to the cation). Additionally, thepolycarbonate arms 102 can comprise areactive end group 206 to facilitate a crosslinkage between the star polymer (e.g., star polymer 100) and another star polymer (e.g., another star polymer 100). The film-forming composition can be toxic to a pathogen (e.g., a Gram-negative bacteria, a Gram-positive bacteria, fungi, and/or yeast). - In one or more embodiments, the film-forming composition can additionally comprise one or more additives to increase efficacy. Example additives can include, but are not limited to: an antimicrobial metal (e.g., nanoparticles of silver, gold, and/or copper), ceramic nanoparticles (e.g., titanium dioxide and/or zinc oxide), antimicrobial metal salts, a pigment, a surfactant, a thickener, an accelerator to speed crosslinking between
star polymers 100, a combination thereof, and/or the like. - In various embodiments, the
star polymers 100 do not readily crosslink with other star polymers (e.g., other star polymers 100) in the presence of the solvent; rather, said crosslinking is performed upon removal of the solvent. Thus, the film-forming composition can exhibit a stable shelf life. Example solvents include, but are not limited to: water, an organic solvent, a combination thereof, and/or the like. -
FIG. 9 illustrates a flow diagram of an example,non-limiting method 900 for forming a surface treated article. Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity. Example articles that can be treated viamethod 900 include, but are not limited to: food packaging, medical devices, floor surfaces, furniture surfaces, wound care instruments (e.g., bandages and/or gauss), building surfaces, plants (e.g., agricultural crops), ground surfaces, farming equipment, beds, sheets, clothes, blankets, shoes, doors, door frames, walls, ceilings, mattresses, light fixtures, facets, switches, sinks, grab rails, remote controls, vanities, computer equipment, carts, trolleys, hampers, bins, a combination thereof, and/or the like. - At 902, the
method 900 can comprise disposing on a surface of an article the film-forming composition described herein. For example, the film-forming composition can comprise thestar polymer 100 dispersed within a solvent. For instance, thestar polymer 100 can comprise greater than or equal to 5 weight percent of the film-forming composition and less than or equal to 20 weight percent of the film-forming composition. Also, thestar polymer 100 can comprise a core having a singlet oxygen generator (e.g., singlet oxygen generator core 104) and that can generate a singlet oxygen species upon irradiation with light. Further, thestar polymer 100 can comprise a plurality of polycarbonate arms (e.g., arm 102) covalently bonded to the core (e.g., singlet oxygen generator core 104). Also, the plurality of polycarbonate arms (e.g., arm 102) can be degradable and comprise a cation (e.g., cationic functional group 204). Thus, the plurality of polycarbonate arms (e.g., arm 102) can have antimicrobial functionality. - The film-forming composition can be disposed on the surface via a variety of techniques including, but not limited to: dipping, spraying, spin coating, brushing, a combination thereof, and/or the like. In various embodiments, disposing the film-forming composition coats the surface of the article with an initial layer of
star polymers 100 that are not crosslinked to other star polymers (e.g., other star polymers 100). At 904, themethod 900 can comprise removing the solvent from the film-forming composition, and thereby, the surface of the coated article. The solvent can be removed via evaporation (e.g., by ambient conditions and/or a drying treatment, such as heated air). Upon removing the solvent, thestar polymers 100 left residing on the surface of the article can begin to crosslink with each other, thereby forming a crosslinked film layer on the surface of the article. - At 906, the
method 900 can optionally include a thermal and/or photochemical treatment of the surface to facilitate crosslinking betweenstar polymers 100. The thickness of the crosslinked film layer of thestar polymers 100 on the surface of the treated article can vary depending on the concentration of the film-forming composition and/or the dispersing technique. In one or more embodiments, themethod 900 can form a crosslinked layer having a thickness substantially equivalent to onestar polymer 100. In some embodiments, themethod 900 can form a crosslinked layer having a thickness substantially equivalent to a plurality ofstar polymers 100. Additionally, the crosslinked film layer can exhibit an opacity greater than or equal to 0% and less than or equal to 100%, with any suitable light absorbing and/or light transmission properties. Further, the crosslinked film layer can be any hue, including, but not limited to, red, yellow, blue or combinations thereof. - In various embodiments, the crosslinked film formed by the
method 900 can adhere to a variety of surface materials including, but not limited to: metal surfaces, glass surfaces, plastic surfaces, ceramic surfaces, wood surfaces, stone surfaces, textile surfaces, paper surfaces, cloth surfaces, concrete surfaces, synthetic fiber surfaces, organic fiber surfaces, a combination thereof, and/or the like. Furthermore, in one or more embodiments the crosslinked film layer can be treated with one or more chemical agents (e.g., alkylating agents) to increase the antimicrobial effect of the crosslinked film layer. In some embodiments, biocompatible forms of thestar polymer 100 can be utilized withmethod 900 to form biocompatible crosslinked films that can surface treat insertable medical devices. - In one or more embodiments, the treated surface comprising the crosslinked film layer can be irradiated with light to facilitate on-demand enhanced antimicrobial functionality. For example, the singlet
oxygen generator core 104 can generate one or more singlet oxygen species in response to the light. Subsequent to being irradiated with light, the crosslinked film layer can be recovered from the article's surface so as to recycle thestar polymer 100. - Thus, in various embodiments a
method 900 of forming a surface treated article can comprise disposing (e.g., at 902) on a surface of an article a film-forming composition. The film-forming composition can comprise a solvent (e.g., water and/or an organic solvent) and a star polymer (e.g., star polymer 100). The star polymer (e.g., star polymer 100) can comprise a singletoxygen generator core 104 and a plurality ofdegradable polycarbonate arms 102. The singletoxygen generator core 104 can be derived from a single oxygen generator molecule (e.g., a porphyrin, a phthalocyanine, a phenothiazine, a xanthene, and/or a quinone). Further, the singletoxygen generator core 104 can comprise one or more linkage groups (e.g., second linkage group 302) to facilitate bonding of thedegradable polycarbonate arms 102. The singletoxygen generator core 104 can generate one or more singlet oxygen species in response to being irradiated with light (e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm). The plurality of degradable polycarbonate arms 102 (e.g., four polycarbonate arms 102) can be covalently bonded to the singlet oxygen generator core 104 (e.g., via the second linkage group 302). The plurality ofpolycarbonate arms 102 can comprise a cationicfunctional group 204 covalently bonded to a molecular backbone 202 (e.g., via the first linkage group 208). The cationicfunctional group 204 can comprise a nitrogen cation (e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation) and/or a phosphorus cation (e.g., a protonated primary phosphine cation, a protonated secondary phosphine cation, a protonated tertiary phosphine cation, a quaternary phosphonium cation). Further, the cationicfunctional group 204 can comprise a hydrophobic group (e.g., bonded to the cation). Additionally, thepolycarbonate arms 102 can comprise areactive end group 206 to facilitate a crosslinking between the star polymer (e.g., star polymer 100) and another star polymer (e.g., another star polymer 100). The film-forming composition can be toxic to a pathogen (e.g., a Gram-negative bacteria, a Gram-positive bacteria, fungi, and/or yeast). Also, themethod 900 can comprise removing the solvent (e.g., at 904) from the surface of the article, and optionally applying a treatment (e.g., at 906) to the film-forming composition (e.g., a thermal treatment and/or a photochemical treatment). -
FIG. 10 illustrates another flow diagram of an example,non-limiting method 1000 of killing a pathogen, preventing the growth of a pathogen, and/or preventing contamination by a pathogen. Repetitive description of like elements employed in other embodiments described herein is omitted for sake of brevity. Example pathogens include, but are not limited to: Gram-negative bacteria, Gram-positive bacteria, fungi, yeast, a combination thereof, and/or the like. - At 1002, the
method 1000 can comprise contacting a pathogen with a polymer (e.g., one or more of thestar polymers 100 and/or a crosslinked film formed on the surface of an article in accordance to method 900). For example, in accordance with various embodiments described herein, the polymer (e.g., a star polymer 100) can comprise a core having a singlet oxygen generator (e.g., singlet oxygen generator core 104) and that can generate a singlet oxygen species upon irradiation with light. Further, the polymer (e.g., star polymer 100) can comprise a plurality of polycarbonate arms (e.g., arm 102) covalently bonded to the core (e.g., singlet oxygen generator core 104). Also, the plurality of polycarbonate arms (e.g., arm 102) can be degradable and comprise a cation (e.g., cationic functional group 204). Thus, the plurality of polycarbonate arms (e.g., arm 102) can have antimicrobial functionality. In various embodiments, upon contact, thestar polymer 100 can disrupt a membrane of the pathogen (e.g., via electrostatic disruption and/or hydrophobic integration). In one or more embodiments, the one ormore star polymers 100 can be located on the surface of an article, whereupon the contacting can comprise a physical meeting of the article's treated surface with the pathogen. In some embodiments, the pathogen can be located on the surface of an article, whereupon the contacting can comprise a physical meeting of the one ormore star polymers 100 with the pathogen. For example, the pathogen can be located on an article and the contacting at 1002 can comprise coating the contaminated article with the film-forming composition described herein. For instance, the pathogen can be located on a crop, wherein the contaminated crop can be sprayed with a film-forming composition comprising thestar polymer 100. - At 1004, the
method 1000 can further comprise irradiating one or more of thestar polymers 100 in contact with the pathogen with light. For example, the light can have a wavelength greater than or equal to 10 nanometers and less than or equal to 750 nanometers. In various embodiments, the one ormore star polymers 100 irradiated with light can respond by generating a singlet oxygen species (e.g., via the singlet oxygen generator core 104), wherein the singlet oxygen species can facilitate degradation of the pathogen. Thus, the antimicrobial effects ofmethod 1000, and thereby the star polymer, can be increased on demand via controlled irradiation of the one or more star polymers with light. - Thus, in one or more embodiments a
method 1000 of killing a pathogen can comprise contacting (e.g., at 1002) the pathogen with a polymer. The polymer (e.g., star polymer 100) can comprise a singletoxygen generator core 104 and a plurality ofdegradable polycarbonate arms 102. The singletoxygen generator core 104 can be derived from a single oxygen generator molecule (e.g., a porphyrin, a phthalocyanine, a phenothiazine, a xanthene, and/or a quinone). Further, the singletoxygen generator core 104 can comprise one or more linkage groups (e.g., second linkage group 302) to facilitate bonding of thedegradable polycarbonate arms 102. The singletoxygen generator core 104 can generate one or more singlet oxygen species in response to being irradiated with light (e.g., light having a wavelength greater than or equal to 10 nm and less than or equal to 750 nm). The plurality of degradable polycarbonate arms 102 (e.g., four polycarbonate arms 102) can be covalently bonded to the singlet oxygen generator core 104 (e.g., via the second linkage group 302). The plurality ofpolycarbonate arms 102 can comprise a cationicfunctional group 204 covalently bonded to a molecular backbone 202 (e.g., via the first linkage group 208). The cationicfunctional group 204 can comprise a nitrogen cation (e.g., a protonated primary amine cation, a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, and/or an imidazolium cation) and/or a phosphorus cation (e.g., a protonated primary phosphine cation, a protonated secondary phosphine cation, a protonated tertiary phosphine cation, a quaternary phosphonium cation). Further, the cationicfunctional group 204 can comprise a hydrophobic group (e.g., bonded to the cation). Additionally, thepolycarbonate arms 102 can comprise areactive end group 206 to facilitate a crosslinkage between the star polymer (e.g., star polymer 100) and another star polymer (e.g., another star polymer 100). Upon contact with the pathogen, the polymer (e.g., star polymer 100) can disrupt a membrane of the pathogen (e.g., via electrostatic disruption and/or hydrophobic integration). Themethod 1000 can further comprise irradiating the polymer with the light (e.g., at 1004), thereby generating the singlet oxygen species via the singletoxygen generator core 104 within the star polymer. - In addition, the term “or” is intended to mean an inclusive “or” rather than an exclusive “or.” That is, unless specified otherwise, or clear from context, “X employs A or B” is intended to mean any of the natural inclusive permutations. That is, if X employs A; X employs B; or X employs both A and B, then “X employs A or B” is satisfied under any of the foregoing instances. Moreover, articles “a” and “an” as used in the subject specification and annexed drawings should generally be construed to mean “one or more” unless specified otherwise or clear from context to be directed to a singular form. As used herein, the terms “example” and/or “exemplary” are utilized to mean serving as an example, instance, or illustration. For the avoidance of doubt, the subject matter disclosed herein is not limited by such examples. In addition, any aspect or design described herein as an “example” and/or “exemplary” is not necessarily to be construed as preferred or advantageous over other aspects or designs, nor is it meant to preclude equivalent exemplary structures and techniques known to those of ordinary skill in the art.
- What has been described above include mere examples of systems, compositions, and methods. It is, of course, not possible to describe every conceivable combination of reagents, products, solvents, and/or articles for purposes of describing this disclosure, but one of ordinary skill in the art can recognize that many further combinations and permutations of this disclosure are possible. Furthermore, to the extent that the terms “includes,” “has,” “possesses,” and the like are used in the detailed description, claims, appendices and drawings such terms are intended to be inclusive in a manner similar to the term “comprising” as “comprising” is interpreted when employed as a transitional word in a claim. The descriptions of the various embodiments have been presented for purposes of illustration, but are not intended to be exhaustive or limited to the embodiments disclosed. Many modifications and variations will be apparent to those of ordinary skill in the art without departing from the scope and spirit of the described embodiments. The terminology used herein was chosen to best explain the principles of the embodiments, the practical application or technical improvement over technologies found in the marketplace, or to enable others of ordinary skill in the art to understand the embodiments disclosed herein.
Claims (25)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/824,250 US10561146B2 (en) | 2017-11-28 | 2017-11-28 | Star polymers with enhanced antimicrobial activity in response to light |
DE112018006058.6T DE112018006058T5 (en) | 2017-11-28 | 2018-11-09 | STAR POLYMERS WITH INCREASED ANTIMICROBIAL ACTIVITY IN RESPONSE TO LIGHT |
PCT/IB2018/058797 WO2019106459A1 (en) | 2017-11-28 | 2018-11-09 | Star polymers with enhanced antimicrobial activity in response to light |
GB2003173.8A GB2580240B (en) | 2017-11-28 | 2018-11-09 | Star polymers with enhanced antimicrobial activity in response to light |
JP2020528011A JP7266351B2 (en) | 2017-11-28 | 2018-11-09 | ANTIMICROBIAL POLYMERS AND METHODS FOR THEIR PRODUCTION, FILM FORMING COMPOSITIONS, AND METHODS FOR FORMING SURFACE TREATED ARTICLES |
US16/738,517 US11930818B2 (en) | 2017-11-28 | 2020-01-09 | Star polymers with enhanced antimicrobial activity in response to light |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/824,250 US10561146B2 (en) | 2017-11-28 | 2017-11-28 | Star polymers with enhanced antimicrobial activity in response to light |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/738,517 Division US11930818B2 (en) | 2017-11-28 | 2020-01-09 | Star polymers with enhanced antimicrobial activity in response to light |
Publications (2)
Publication Number | Publication Date |
---|---|
US20190159456A1 true US20190159456A1 (en) | 2019-05-30 |
US10561146B2 US10561146B2 (en) | 2020-02-18 |
Family
ID=66633916
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/824,250 Expired - Fee Related US10561146B2 (en) | 2017-11-28 | 2017-11-28 | Star polymers with enhanced antimicrobial activity in response to light |
US16/738,517 Active 2040-12-09 US11930818B2 (en) | 2017-11-28 | 2020-01-09 | Star polymers with enhanced antimicrobial activity in response to light |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/738,517 Active 2040-12-09 US11930818B2 (en) | 2017-11-28 | 2020-01-09 | Star polymers with enhanced antimicrobial activity in response to light |
Country Status (5)
Country | Link |
---|---|
US (2) | US10561146B2 (en) |
JP (1) | JP7266351B2 (en) |
DE (1) | DE112018006058T5 (en) |
GB (1) | GB2580240B (en) |
WO (1) | WO2019106459A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10561146B2 (en) * | 2017-11-28 | 2020-02-18 | International Business Machines Corporation | Star polymers with enhanced antimicrobial activity in response to light |
FR3090271B1 (en) * | 2018-12-19 | 2021-03-05 | Commissariat A L’Energie Atomique Et Aux Energies Alternatives Cea | PROCESS FOR THE PREPARATION OF A BIOCIDAL, BACTERICIDAL AND / OR BACTERIOSTATIC MATERIAL |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2408265A (en) * | 2003-11-21 | 2005-05-25 | Univ Sheffield | Water-soluble hyperbranched polymer porphyrins |
US8765098B2 (en) * | 2010-03-30 | 2014-07-01 | International Business Machines Corporation | Star polymers, methods of preparation thereof, and uses thereof |
US8945513B2 (en) | 2011-03-18 | 2015-02-03 | International Business Machines Corporation | Star polymer nanoshells and methods of preparation thereof |
US8709466B2 (en) | 2011-03-31 | 2014-04-29 | International Business Machines Corporation | Cationic polymers for antimicrobial applications and delivery of bioactive materials |
US9040034B2 (en) * | 2013-04-09 | 2015-05-26 | International Business Machines Corporation | Vitamin functionalized gel-forming block copolymers for biomedical applications |
US9357772B2 (en) * | 2013-04-09 | 2016-06-07 | International Business Machines Corporation | Antimicrobial cationic polycarbonates |
US20140370064A1 (en) | 2013-06-16 | 2014-12-18 | International Business Machines Corporation | Film-forming compositions of self-crosslinkable nanogel star polymers |
CN104861172B (en) | 2015-04-28 | 2017-04-05 | 同济大学 | A kind of preparation method of the star copolymer with fluorescent effect, pH responses and temperature-responsive with porphyrin as core |
US9854806B2 (en) | 2015-05-19 | 2018-01-02 | International Business Machines Corporation | Antimicrobial guanidinium and thiouronium functionalized polymers |
US10561146B2 (en) * | 2017-11-28 | 2020-02-18 | International Business Machines Corporation | Star polymers with enhanced antimicrobial activity in response to light |
-
2017
- 2017-11-28 US US15/824,250 patent/US10561146B2/en not_active Expired - Fee Related
-
2018
- 2018-11-09 JP JP2020528011A patent/JP7266351B2/en active Active
- 2018-11-09 WO PCT/IB2018/058797 patent/WO2019106459A1/en active Application Filing
- 2018-11-09 DE DE112018006058.6T patent/DE112018006058T5/en active Pending
- 2018-11-09 GB GB2003173.8A patent/GB2580240B/en active Active
-
2020
- 2020-01-09 US US16/738,517 patent/US11930818B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP7266351B2 (en) | 2023-04-28 |
DE112018006058T5 (en) | 2020-10-01 |
US10561146B2 (en) | 2020-02-18 |
US11930818B2 (en) | 2024-03-19 |
GB2580240A (en) | 2020-07-15 |
WO2019106459A1 (en) | 2019-06-06 |
GB2580240B (en) | 2020-12-16 |
GB202003173D0 (en) | 2020-04-22 |
JP2021504509A (en) | 2021-02-15 |
US20200146296A1 (en) | 2020-05-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Cheng et al. | Polymer microspheres with permanent antibacterial surface from surface-initiated atom transfer radical polymerization | |
Muñoz-Bonilla et al. | Poly (ionic liquid) s as antimicrobial materials | |
Gour et al. | Anti‐I nfectious Surfaces Achieved by Polymer Modification | |
Yang et al. | Smart antibacterial surface made by photopolymerization | |
Alamri et al. | Biocidal polymers: synthesis and antimicrobial properties of benzaldehyde derivatives immobilized onto amine-terminated polyacrylonitrile | |
Koufakis et al. | Film properties and antimicrobial efficacy of quaternized PDMAEMA brushes: short vs long alkyl chain length | |
US10584191B2 (en) | Antimicrobial star polymers with light-activated enhanced antimicrobial activity | |
US11930818B2 (en) | Star polymers with enhanced antimicrobial activity in response to light | |
Yang et al. | Biocompatible graphene-based nanoagent with NIR and magnetism dual-responses for effective bacterial killing and removal | |
Arora et al. | Polymer based antimicrobial coatings as potential biomaterial: A review | |
US10975260B2 (en) | Monomers, polymers and coating formulations that comprise at least one N-halamine precursor, a cationic center and a coating incorporation group | |
Huang et al. | Progress for the development of antibacterial surface based on surface modification technology | |
Wang et al. | One-pot quaternization of dual-responsive poly (vinyl alcohol) with AIEgens for pH-switchable imaging and killing of bacteria | |
JP7249718B2 (en) | Polymer with antibacterial function | |
EP1182928B1 (en) | Method for producing microbicidal surfaces by immobilizing inherently microbicidally active macromolecules | |
CN111491981B (en) | Hydrophilic polymers with antimicrobial function | |
Yao et al. | Quaternary Ammonium Compounds and Their Composites in Antimicrobial Applications | |
JP2022179510A (en) | Monomer compositions with antimicrobial functionality | |
Sun et al. | Poly (phosphonium)-Functionalized Double-Armed β-CD Antimicrobial Material via RAFT | |
Grigoras | Polymeric antimicrobials with quaternary ammonium moieties | |
Thapliyal et al. | Synthesis Mechanisms for Antimicrobial Polymeric Coatings | |
Saúde et al. | Functionalization of nanostructures for antibiotic improvement: an interdisciplinary approach | |
US10687528B2 (en) | Antimicrobial polymers with enhanced functionalities | |
Rodríguez-Hernández et al. | Nano-Micro Polymeric Structures with Antimicrobial Activity in Solution | |
Parcheta et al. | Preparation and Functionalization of Polymers with Antibacterial Properties—Review of the Recent Developments. Materials 2023, 16, 4411 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH, SINGA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHIN, WILLY;VOO, ZHI XIANG;YANG, YI YAN;SIGNING DATES FROM 20171120 TO 20171122;REEL/FRAME:044238/0207 Owner name: INTERNATIONAL BUSINESS MACHINES CORPORATION, NEW Y Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HEDRICK, JAMES L.;FINE NATHEL, NOAH FREDERICK;PIUNOVA, VICTORIA A.;SIGNING DATES FROM 20171117 TO 20171120;REEL/FRAME:044237/0968 Owner name: INTERNATIONAL BUSINESS MACHINES CORPORATION, NEW YORK Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HEDRICK, JAMES L.;FINE NATHEL, NOAH FREDERICK;PIUNOVA, VICTORIA A.;SIGNING DATES FROM 20171117 TO 20171120;REEL/FRAME:044237/0968 Owner name: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH, SINGAPORE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHIN, WILLY;VOO, ZHI XIANG;YANG, YI YAN;SIGNING DATES FROM 20171120 TO 20171122;REEL/FRAME:044238/0207 |
|
FEPP | Fee payment procedure |
Free format text: ENTITY STATUS SET TO UNDISCOUNTED (ORIGINAL EVENT CODE: BIG.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NON FINAL ACTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NOTICE OF ALLOWANCE MAILED -- APPLICATION RECEIVED IN OFFICE OF PUBLICATIONS |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NOTICE OF ALLOWANCE MAILED -- APPLICATION RECEIVED IN OFFICE OF PUBLICATIONS |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
FEPP | Fee payment procedure |
Free format text: MAINTENANCE FEE REMINDER MAILED (ORIGINAL EVENT CODE: REM.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
LAPS | Lapse for failure to pay maintenance fees |
Free format text: PATENT EXPIRED FOR FAILURE TO PAY MAINTENANCE FEES (ORIGINAL EVENT CODE: EXP.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |
|
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 20240218 |